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Encyclopedia > Vanillin
Vanillin
Vanillin
General
Systematic name 4-Hydroxy-3-methoxybenzaldehyde
Other names Vanilin
Vanillic aldehyde
Methyl vanillin
Molecular formula C8H8O3
SMILES O=CC1=CC(OC)=C(O)C=C1
Molar mass 152.14 g/mol
Appearance White or lightly yellow solid
(usually in needles)
CAS number [121-33-5]
Properties
Density and phase 1.056 g/cm3, solid
Solubility in water 1 g/100 ml (25°C)
Melting point 80-81°C (353-354 K)
Boiling point 285°C (558 K)
Acidity (pKa) 7.396
Viscosity  ? cP at ?°C
Hazards
MSDS External MSDS
Main hazards May cause irritation to skin,
eyes, and respiratory tract
NFPA 704

Wikipedia does not have an article with this exact name. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is defined as mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... In chemistry and biochemistry, the acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydronium ions from an acid. ... The related Category:Units of viscosity has been nominated for deletion, merging, or renaming. ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ...

1
1
0
 
Flash point 147°C
R/S statement R: R22.
S: S24/25.
RTECS number YW5775000
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data 1H NMR 13C NMR
Related compounds
Related compounds Eugenol, Anisaldehyde
Phenol
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Infobox disclaimer and references

Vanillin, methyl vanillin, or 4-hydroxy-3-methoxybenzaldehyde, is an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, ether, and alcohol. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is used as a flavoring agent in foods, beverages, and pharmaceuticals. The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index (or index of refraction) of a material is the factor by which the phase velocity of electromagnetic radiation is slowed in that material, relative to its velocity in a vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Download high resolution version (619x670, 7 KB)1H (proton) NMR spectrum for 0. ... Download high resolution version (619x670, 13 KB)13C NMR spectrum for 0. ... Eugenol (C10H12O2), is an allyl chain-substituted guaiacol, i. ... Anisaldehyde, or anisic aldehyde or 4-methoxybenzaldehyde, is an organic compound that consists of a benzene ring substituted with an aldehyde and a methoxy group. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... In ecology functional groups are collections of organisms based on morphological, physiological, behavioral, biochemical, or environmental responses or on trophic criteria. ... An aldehyde. ... Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... Functional group of an alcohol molecule. ... Vanilla is a flavoring derived from orchids in the genus Vanilla. ... Flavouring (CwE) or flavoring (AmE) is a product which is added to food in order to change or augment its taste. ...


Methyl vanillin is used by the food industry as well as ethyl vanillin. The ethyl is more expensive but has a stronger note, and differs by having an ethoxy group (-O-CH2CH3) instead of a methoxy group (-O-CH3).


Natural vanilla extract is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made from either the petrochemical guaiacol, or from lignin, a natural constituent of wood which is a byproduct of the paper industry. Vanilla is a flavoring derived from orchids in the genus Vanilla. ... Eugenol (C10H12O2), is an allyl chain-substituted guaiacol, i. ... Petrochemicals are chemical products made from raw materials of petroleum (hydrocarbon) origin. ... Chemical structure of guaiacol Guaiacol, or 2-methoxyphenol, is a natural organic compound with the molecular formula C7H8O2. ... Lignin (sometimes lignen) is a chemical compound that is most commonly derived from wood and is an integral part of the cell walls of plants, especially in tracheids, xylem fibres and sclereids. ... Trunks A tree trunk as found at the Veluwe, The Netherlands Wood is a solid material derived from woody plants, notably trees but also shrubs. ... An International Paper mill in South Carolina The global pulp and paper industry is dominated by North American (United States, Canada), northern European (Sweden, Finland) and East Asian countries (such as Japan). ...


Lignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than oil-based flavoring; the difference is due to the presence of acetovanillone in the lignin-derived product, an impurity not found in vanillin synthesized from guaiacol.[1]

Contents

History

Vanilla was cultivated as a flavoring by pre-Columbian Mesoamerican peoples; at the time of their conquest by Hernándo Cortés, the Aztecs used it as a flavoring for chocolate. Europeans became aware of both chocolate and vanilla around the year 1520.[2] Hernán Cortés Hernán Cortés, marqués del Valle de Oaxaca (1485–December 2, 1547) was the conquistador who conquered Mexico for Spain. ... The word Aztec is usually used as a historical term, although some contemporary Nahuatl speakers would consider themselves Aztecs. ... Chocolate most commonly comes in dark, milk, and white varieties, with cocoa solids contributing to the brown coloration. ...


Vanillin was first isolated as a relatively pure substance in 1858 by Nicolas-Theodore Gobley, who obtained it by evaporating a vanilla extract to dryness, and recrystallizing the resulting solids from hot water.[3] In 1874, the german scientists Ferdinand Tiemann and Wilhelm Haarmann deduced its chemical structure, at the same time finding a synthesis for vanillin from coniferin, a glycoside of isoeugenol found in pine bark,[4] and in 1876, Karl Reimer synthesized vanillin from guaiacol.[5] By the late 19th century, semisynthetic vanillin derived from the eugenol found in clove oil was commercially available.[6] Nicolas-Theodore Gobley (b. ... Insulin crystals Recrystallization is an essentially physical process that has meanings in chemistry, metallurgy and geology. ... A glycoside is a molecule where a sugar group is bonded through its anomeric carbon to a nonsugar group by either an oxygen or a nitrogen atom. ... Subgenera Subgenus Strobus Subgenus Ducampopinus Subgenus Pinus See Pinus classification for complete taxonomy to species level. ... Chemical structure of guaiacol Guaiacol, or 2-methoxyphenol, is a natural organic compound with the molecular formula C7H8O2. ... Eugenol (C10H12O2), is an allyl chain-substituted guaiacol, i. ... Binomial name Syzygium aromaticum (L.) Merrill & Perry A single dried clove flower bud Cloves (Syzygium aromaticum, syn. ...


Synthetic vanillin became significantly more available in the 1930s, when production from clove oil was supplanted by production from the lignin-containing waste produced by the Kraft process for preparing wood pulp for the paper industry. By 1981, a single pulp and paper mill in Ontario supplied 60% of the world market for synthetic vanillin.[7] However, subsequent developments in the wood pulp industry have made its lignin wastes less attractive as a raw material for vanillin synthesis. While some vanillin is still made from lignin wastes, most synthetic vanillin is today synthesized in a two-step process from the petrochemical precursors guaiacol and glyoxylic acid.[8] Lignin (sometimes lignen) is a chemical compound that is most commonly derived from wood and is an integral part of the cell walls of plants, especially in tracheids, xylem fibres and sclereids. ... The Kraft process is used in production of paper pulp and involves the use of caustic sodium hydroxide and sodium sulfide to extract the lignin from the wood fiber in large vats called digesters. ... A blank sheet of paper Paper is a commodity of thin material produced by the amalgamation of fibers, typically vegetable fibers composed of cellulose, which are subsequently held together by hydrogen bonding. ... Chemical structure of guaiacol Guaiacol, or 2-methoxyphenol, is a natural organic compound with the molecular formula C7H8O2. ... Glyoxylic acid or oxoacetic acid is an organic compound with the chemical formula C2H2O3 and structure HOC-COOH. Other synonyms are formylformic acid and oxoethanoic acid. ...


Beginning in 2000, Rhodia began marketing biosynthetic vanillin prepared by the action of microorganisms on ferulic acid extracted from rice bran. At $700/kg, this product, sold under the trademarked name Rhovanil Natural, is not cost-competitive with petrochemical vanillin, which sells for around $15/kg.[9] However, unlike vanillin synthesized from lignin or guaiacol, it can be labeled as a natural flavoring. Rhodia is an international chemical company based in Paris, France. ... Furelic acid protects our cells form ultraviolet rays. ... Species Oryza glaberrima Oryza sativa The planting of rice is often a labour-intensive process Terrace of rice paddies in Yunnan Province, southern China. ... wheat bran Bran is the hard outer layer of cereal grains, and consists of combined aleurone and pericarp. ...


Occurrence

Vanillin is most prominent as the principal flavor and aroma compound in vanilla. Cured vanilla pods contain approximately 2% by dry weight vanillin; on cured pods of high quality, relatively pure vanillin may be visible as a white dust or "frost" on the exterior of the pod.


At smaller concentrations, vanillin contributes to the flavor and aroma profiles of foodstuffs as diverse as olive oil,[10] butter,[11] and raspberry[12] and lychee[13] fruits. Aging in oak barrels imparts vanillin to some wines and spirits.[14] In other foods, heat treatment evolves vanillin from other chemicals. In this way, vanillin contributes to the flavor and aroma of coffee,[15] maple syrup,[16] and whole grain products including corn tortillas[17] and oatmeal.[18] A bottle of olive oil. ... Butter is commonly sold in sticks (pictured) or blocks, and frequently served with the use of a butter knife. ... Binomial name Rubus idaeus L. The Raspberry or Red Raspberry (Rubus idaeus) is a plant that produces a tart, sweet, red composite fruit in summer or early autumn. ... Binomial name Litchi chinensis Sonn. ... Species See List of Quercus species The term oak can be used as part of the common name of any of several hundred species of trees and shrubs in the genus Quercus, and some related genera, notably Cyclobalanopsis and Lithocarpus. ... A glass of red wine This article is about the alcoholic beverage. ... Various distilled beverages in a Spanish bar A distilled beverage is a liquid, meant for consumption, containing ethyl alcohol (ethanol) purified by distillation from a fermented substance such as fruit, vegetables, or grain. ... A cup of coffee Workers sorting and pulping coffee beans in Guatemala Coffee is a widely consumed beverage prepared from the roasted seeds—commonly referred to as beans—of the coffee plant. ... This article does not cite its references or sources. ... This article or section does not cite its references or sources. ... Two cooked flour tortillas. ... Oatmeal is a product made by processing oats. ...


Production

These green seed pods contain vanillin only in its glycoside form, and lack the characteristic odor of vanilla.
These green seed pods contain vanillin only in its glycoside form, and lack the characteristic odor of vanilla.

ImageMetadata File history File links Download high resolution version (525x700, 289 KB) Description: Vanilla fragrans, Bras-Panon, La Réunion, nov. ... ImageMetadata File history File links Download high resolution version (525x700, 289 KB) Description: Vanilla fragrans, Bras-Panon, La Réunion, nov. ...

Natural production

Natural vanillin is extracted from the seed pods of Vanilla planifola, a vining orchid native to Mexico, but now grown in tropical areas around the globe. Madagascar is presently the largest producer of natural vanillin. Vanilla is a flavoring derived from orchids in the genus Vanilla. ... A curling tendril A vine is any plant of genus Vitis (the grape plants) or, by extension, any similar climbing or trailing plant. ... Orchid re-directs here; for alternate uses see Orchid (disambiguation) Genera Over 800 See List of Orchidaceae genera. ...


As harvested, the green seed pods contain vanillin in the form of its β-D-glycoside; the green pods do not have the flavor or odor of vanilla.[19] After being harvested, their flavor is developed by a months-long curing process, the details of which vary among vanilla-producing regions, but in broad terms it proceeds as follows: A glycoside is a molecule where a sugar group is bonded through its anomeric carbon to a nonsugar group by either an oxygen or a nitrogen atom. ...


First, the seed pods are blanched in hot water, to arrest the processes of the living plant tissues. Then, for 1–2 weeks, the pods are alternately sunned and sweated: during the day, they are laid out in the sun, and each night, wrapped in cloth and packed in airtight boxes to sweat. During this process, the pods become a dark brown, and enzymes in the pod release vanillin as the free molecule. Finally, the pods are dried and further aged for several months, during which time their flavors further develop. Several methods have been described for curing vanilla in days rather than months, although they have not been widely developed in the natural vanilla industry,[20] with its focus on producing a premium product by established methods, rather than on innovations that might alter the product's flavor profile. Wikibooks Cookbook has more about this subject: Blanching Blanching is a cooking term that describes a process of food preparation wherein the food substance is rapidly plunged into boiling water and then removed after a brief, timed interval and then plunged into iced water or placed under cold running water. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ...


Vanillin accounts for about 2% of the dry weight of cured vanilla beans, and is the chief among about 200 other flavor compounds found in vanilla.


Chemical synthesis

The demand for vanilla flavoring has long exceeded the supply of vanilla beans. As of 2001, the annual demand for vanillin was 12,000 tons, but only 1800 tons of natural vanillin were produced.[21] The remainder was produced by chemical synthesis. Vanillin was first synthesized from eugenol (found in oil of clove) in 1874–75, less than 20 years after it was first identified and isolated. Vanillin was commercially produced from eugenol until the 1920s.[22] Later it was synthesized from lignin-containing sulfite liquor, a byproduct of wood pulp processing in paper manufacture.[23] Counter-intuitively, even though it uses waste materials, the lignin process is no longer popular because of environmental concerns, and today most vanillin is produced from the petrochemical raw material guaiacol.[24] Several routes exist for synthesizing vanillin from guaiacol.[25] At present, the most significant of these is the two-step process practiced by Rhodia since the 1970s, in which guaiacol reacts with glyoxylic acid by electrophilic aromatic substitution. The resulting vanilmandelic acid is then converted to vanillin by oxidative decarboxylation.[26] 2001 is a common year starting on Monday of the Gregorian calendar, and also: The International Year of the Volunteer The United Nations Year of Dialogue Among Civilizations Events January January 1 - A black monolith measuring approximately nine feet tall appears in Seattles Magnuson Park, placed by an anonymous... In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product, or several products. ... Eugenol (C10H12O2), is an allyl chain-substituted guaiacol, i. ... Binomial name Syzygium aromaticum (L.) Merrill & Perry A single dried clove flower bud Cloves (Syzygium aromaticum, syn. ... Lignin (sometimes lignen) is a chemical compound that is most commonly derived from wood and is an integral part of the cell walls of plants, especially in tracheids, xylem fibres and sclereids. ... International Paper Company Wood pulp is the most common material used to make paper. ... Petrochemicals are chemical products made from raw materials of petroleum (hydrocarbon) origin. ... Chemical structure of guaiacol Guaiacol, or 2-methoxyphenol, is a natural organic compound with the molecular formula C7H8O2. ... Rhodia is a planet in The Stars, Like Dust by Isaac Asimov. ... Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, in an aromatic system is replaced by an electrophile. ...


Uses

The largest single use of vanillin is as a flavoring, usually in sweet foods. The ice cream and chocolate industries together comprise 75% of the market for vanillin as a flavoring, with smaller amounts being used in confections and baked goods.[27] Sweetness is one of the five basic tastes, and is almost universally regarded as a pleasurable experience. ... Missing image Ice cream is often served on a stick Boxes of ice cream are often found in stores in a display freezer. ... Chocolate most commonly comes in dark, milk, and white varieties, with cocoa solids contributing to the brown coloration. ... The term confectionery refers to food items rich in sugar. ... Wikibooks Cookbook has more about this subject: Baking Baking is the technique of cooking food in an oven by dry heat applied evenly throughout the oven. ...


Vanillin is also used in the fragrance industry, in perfumes, and to mask unpleasant odors or tastes in medicines, livestock fodder, and cleaning products.[28] Perfume is a mixture of fragrant essential oils and aroma compounds, fixatives, and solvents used to give the human body, objects, and living spaces a pleasant smell. ... Fodder growing from barley In agriculture, fodder or animal feed is any foodstuff that is used specifically to feed livestock, such as cattle, sheep, chickens and pigs. ...


Vanillin has been used as a chemical intermediate in the production of pharmaceuticals and other fine chemicals. In 1970, more than half the world's vanillin production was used in the synthesis of other chemicals,[29] but as of 2004 this use accounts for only 13% of the market for vanillin.[30] Pharmacology (in Greek: pharmacon is drug, and logos is science) is the study of how chemical substances interfere with living systems. ... In drug manufacture, fine chemicals are pure, single chemical substances that are produced by chemical reactions. ...


Vanillin can also be found in bottles of Buckfast Tonic Wine (made by the monks of Buckfast Abbey) sold in the United Kingdom. It is not however found in the bottles sold in the Republic of Ireland.[citation needed] Buckfast Tonic Wine, commonly known as Buckfast, Buckie or Bucky is a tonic wine produced by Buckfast Abbey in Devon, south west England. ... Buckfast Abbey in Buckfastleigh, Devon is one of a small number of active monasteries in Britain today. ...


References

  • Adahchour, Mohamed; René J. J. Vreuls, Arnold van der Heijden and Udo A. Th. Brinkman (1999). "Trace-level determination of polar flavour compounds in butter by solid-phase extraction and gas chromatography–mass spectrometry". Journal of Chromatography A 844 (1-2): 295-305. DOI:10.1016/S0021-9673(99)00351-9. 
  • Blank, Imre; Alina Sen, and Werner Grosch (1992). "Potent odorants of the roasted powder and brew of Arabica coffee". Zeitschrift für Lebensmittel-Untersuchung und -Forschung A 195 (3): 239-245. DOI:10.1007/BF01202802. 
  • Brenes, Manuel; Aranzazu García, Pedro García, José J. Rios, and Antonio Garrido (1999). "Phenolic Compounds in Spanish Olive Oils". Journal of Agricultural and Food Chemistry 47 (9): 3535-3540. DOI:10.1021/jf990009o. 
  • Buttery, Ron G.; and Louisa C. Ling (1995). "Volatile Flavor Components of Corn Tortillas and Related Products". Journal of Agricultural and Food Chemistry 43 (7): 1878-1882. DOI:10.1021/jf00055a023. 
  • Dignum, Mark J. W.; Josef Kerlera, and Rob Verpoorte (2001). "Vanilla Production: Technological, Chemical, and Biosynthetic Aspects". Food Reviews International 17 (2): 119–120. DOI:10.1081/FRI-100000269. Retrieved on 2006-09-09. 
  • Esposito, Lawrence J..; K. Formanek, G. Kientz, F. Mauger, V. Maureaux, G. Robert, and F. Truchet (1997). "Vanillin". Kirk-Othmer Encyclopedia of Chemical Technology, 4th edition 24: 812–825. New York: John Wiley & Sons.
  • Fund for Research into Industrial Development, Growth and Equity (FRIDGE) (2004). Study into the Establishment of an Aroma and Fragrance Fine Chemicals Value Chain in South Africa, Part Three: Aroma Chemicals Derived from Petrochemical Feedstocks. National Economic Development and Labor Council. 
  • Gobley, N.-T. (1858). "Recherches sur le principe odorant de la vanille". Journal de Pharmacie et de Chimie 34: 401-405. 
  • Guth, Helmut; and Werner Grosch (1995). "Odorants of extrusion products of oat meal: Changes during storage". Zeitschrift für Lebensmittel-Untersuchung und -Forschung A 196 (1): 22-28. DOI:10.1007/BF01192979. 
  • Hocking, Martin B. (September 1997). "Vanillin: Synthetic Flavoring from Spent Sulfite Liquor" (PDF). Journal of Chemical Education 74 (9): 1055. Retrieved on 2006-09-09. 
  • Kermasha, S.; M. Goetghebeur, and J. Dumont (1995). "Determination of Phenolic Compound Profiles in Maple Products by High-Performance Liquid Chromatography". Journal of Agricultural and Food Chemistry 43 (3): 708-716. DOI:10.1021/jf00051a028. 
  • Lampman, Gary M.; Jennifer Andrews, Wayne Bratz, Otto Hanssen, Kenneth Kelley, Dana Perry, and Anthony Ridgeway (1977). "Preparation of vanillin from eugenol and sawdust". Journal of Chemical Education 54 (12): 776-778. 
  • Ong, Peter K. C.; Terry E. Acree (1998). "Gas Chromatography/Olfactory Analysis of Lychee (Litchi chinesis Sonn.)". Journal of Agricultural and Food Chemistry 46 (6): 2282-2286. DOI:10.1021/jf9801318. 
  • Reimer, K. (1876). "Ueber eine neue Bildungsweise aromatischer Aldehyde". Berichte der deutschen chemischen Gesellschaft 9 (1): 423-424. DOI:10.1002/cber.187600901134. 
  • Roberts, Deborah D.; Terry E. Acree (1996). "Effects of Heating and Cream Addition on Fresh Raspberry Aroma Using a Retronasal Aroma Simulator and Gas Chromatography Olfactometry". Journal of Agricultural and Food Chemistry 44 (12): 3919-3925. DOI:10.1021/jf950701t. 
  • Rouhi, A. Maureen (2003). "Fine Chemicals Firms Enable Flavor And Fragrance Industry". Chemical and Engineering News 81 (28): 54. 
  • Tiemann, Ferd.; Wilh. Haarmann. "Ueber das Coniferin und seine Umwandlung in das aromatische Princip der Vanille". Berichte der Deutschen Chemischen Gesellschaft 7 (1): 608-623. DOI:10.1002/cber.187400701193. 
  • Van Ness, J. H.. (1983). "Vanillin". Kirk-Othmer Encyclopedia of Chemical Technology, 3rd edition 23: 704–717. New York: John Wiley & Sons.
  • Viriot, Carole; Augustin Scalbert, Catherine Lapierre, and Michel Moutounet (1993). "Ellagitannins and lignins in aging of spirits in oak barrels". Journal of Agricultural and Food Chemistry 41 (11): 1872-1879. DOI:10.1021/jf00035a013. 
  • Walton, Nicholas J.; Melinda J. Mayer, and Arjan Narbad (July 2003). "Vanillin". Phytochemistry 63 (5): 505–515. DOI:10.1016/S0031-9422(03)00149-3. 

A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... For the Manfred Mann album, see 2006 (album). ... September 9 is the 252nd day of the year (253rd in leap years). ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... For the Manfred Mann album, see 2006 (album). ... September 9 is the 252nd day of the year (253rd in leap years). ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

Notes

  1. ^ According to Esposito 1997, blind taste-testing panels cannot distinguish between the flavors of synthetic vanillin from lignin and from guaicol, but can distinguish the odors of these two types of synthetic vanilla extracts. Guaiacol vanillin, adulterated with acetovanillone, has an odor indistinguishable from lignin vanillin.
  2. ^ Esposito 1997
  3. ^ Gobley 1858
  4. ^ Tiemann 1874
  5. ^ Reimer 1876
  6. ^ According to Hocking 1997, synthetic vanillin was sold commercially in 1874, the same year Tiemann and Haarmann's original synthesis was published. Haarmann & Reimer, one of the corporate ancestors of the modern flavor and aroma manufacturer Symrise, was in fact established in 1874. However, Esposito 1997 claims that synthetic vanillin first became available in 1894 when Rhône-Poulenc (since 1998, Rhodia) entered the vanillin business. If the former claim is correct, the authors of the latter article, being employees of Rhône-Poulenc, may have been unaware of any previous vanillin manufacture.
  7. ^ Hocking 1997
  8. ^ Esposito 1997
  9. ^ Rouhi 2003
  10. ^ Brenes 1999
  11. ^ Adahchour 1999
  12. ^ Roberts 1996
  13. ^ Ong 1998
  14. ^ Viriot 1993
  15. ^ Blank 1992
  16. ^ Kermasha 1995
  17. ^ Buttery 1995
  18. ^ Guth 1993
  19. ^ Walton 2003
  20. ^ Dignum 2001 reviews several such proposed innovations in vanilla processing, including processes in which the seed pods are chopped, frozen, warmed by a heat source other than the sun, or crushed and treated by various enzymes. Whether or not these procedures produce a product whose taste is comparable to traditionally prepared natural vanilla, many of them are incompatible with the customs of the natural vanilla market, in which the vanilla beans are sold whole, and graded by, among other factors, their length.
  21. ^ Dignum 2001
  22. ^ Hocking 1997. This chemical process can be conveniently carried out on the laboratory scale using the procedure described by Lampman 1977.
  23. ^ Hocking 1997
  24. ^ Hocking 1997
  25. ^ Van Ness 1983
  26. ^ Esposito 1997
  27. ^ FRIDGE 2004, p. 33
  28. ^ Esposito 1997
  29. ^ Hocking 1997
  30. ^ FRIDGE 2004, p. 32

Symrise is a major producer of flavors and fragrances with sales of € 1,138. ... Rhodia is a planet in The Stars, Like Dust by Isaac Asimov. ...

External links

  • Vanillin 3D view and pdb-file
  • Links to external chemical sources

  Results from FactBites:
 
Dating the shroud by its vanillin content (1530 words)
Thus, by measuring the amount of vanillin remaining on the cloth, one might be able to estimate the age of the cloth.
Rogers believes that vanillin is detectable in the sample taken for radiocarbon testing.
He believes that vanillin is also present in the "Holland cloth" used to patch the shroud.
Vanillin - Vanilla (356 words)
Vanillin is also used in the preparation of pharmaceutical drugs for Parkinson's disease and hypertension.
Vanillin (for artificial vanilla) can also be produced as a byproduct of the paper and pulp product industry through the oxidative breakdown of lignin, a complex polymer, a non-carbohydrate constituent of plant material.
Of particular interest, the Shroud of Turin does not test positive for vanillin except in one particular place, the place from which the carbon 14 sample were taken in 1988 for radiocarbon dating.
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