ChemicalBook Deutsch Chinese English Japanese Korea
ChemicalBook > Produktkatalog >Aktive pharmazeutische Wirkstoffe (APIs) >Nervensystem Drogen >Antiepileptika (AEDs) >Vanillin

Vanillin Produkt Beschreibung

Englisch Name:Vanillin
Zimco;Lioxin;Vanilin;VANILLA;VANILLIN;Vinillin;Rhovanil;VANILLINE;FEMA 3107;VANILLINUM
Vanillin physikalisch-chemischer Eigenschaften
Schmelzpunkt:: 81-83 °C(lit.)
Siedepunkt:: 170 °C15 mm Hg(lit.)
Dichte: 1.06
Dampfdichte: 5.3 (vs air)
Dampfdruck: >0.01 mm Hg ( 25 °C)
Brechungsindex: 1.4850 (estimate)
Flammpunkt:: 147 °C
storage temp. : Refrigerator
Löslichkeit: methanol: 0.1 g/mL, clear
pka: pKa 7.396±0.004(H2O I = 0.00 t = 25.0±1.0) (Reliable)
Aggregatzustand: Crystalline Powder
Farbe: White to pale yellow
PH: 4.3 (10g/l, H2O, 20℃)
Wasserlöslichkeit: 10 g/L (25 ºC)
Sensitive : Air & Light Sensitive
Merck : 14,9932
JECFA Number: 889
BRN : 472792
Stabilität:: Stable. May discolour on exposure to light. Moisture-sensitive. Incompatible with strong oxidizing agents, perchloric acid.
CAS Datenbank: 121-33-5(CAS DataBase Reference)
NIST chemische Informationen: Benzaldehyde, 4-hydroxy-3-methoxy-(121-33-5)
EPA chemische Informationen: Benzaldehyde, 4-hydroxy-3-methoxy-(121-33-5)
Kennzeichnung gefährlicher: Xn,Xi
R-Sätze:: 22-36/37/38-36
S-Sätze:: 24/25-22-37/39-26-36/37/39
RIDADR : UN 2924 3/8/PG II
WGK Germany : 1
RTECS-Nr.: YW5775000
Selbstentzündungstemperatur: >400 °C
TSCA : Yes
HazardClass : 3/8
PackingGroup : II
HS Code : 29124100
Giftige Stoffe Daten: 121-33-5(Hazardous Substances Data)
Toxizität: LD50 orally in rats, guinea pigs: 1580, 1400 mg/kg (Jenner)

Vanillin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S22:Staub nicht einatmen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Aussehen Eigenschaften
C8H8O3; 4-Hydroxy-3-methoxybenzaldehyd. Fast weißes Pulver mit aromatischem, charakteristischem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich beim Verschlucken.
LD50 (oral, Ratte): 1580 mg/kg.
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Staubschutz.
Verhalten im Gefahrfall
Trocken aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Wasser, Pulver, Schaum.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 15 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Reichlich Wasser trinken. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
Ersthelfer: siehe gesonderten Anschlag

Sachgerechte Entsorgung
Als feste Laborchemikalienabfälle.
Chemische Eigenschaften
White, crystalline needles; sweetish smell. Soluble in 125 parts water, in 20 parts glycerol, and in 2 parts 95% alcohol; soluble in chloroform and ether. Combustible.
Chemische Eigenschaften
White or cream, crystalline needles or powder with characteristic vanilla odor and sweet taste.
Chemische Eigenschaften
A great variety of vanilla plants bearing the vanilla pods, or siliques, exist. Those mentioned above are the most important species. Of special value are those cultivated in Mexico, Madagascar, Java, Tahiti, the Comoro Islands and Réunion. The cultivation of vanilla beans is very long and laborious. The plant is a perennial herbaceous vine that grows up to 25 m in height and needs suitable supports in order to grow. Fecundation of flowers is performed (November to December) by perforating the membrane that separates the pollen from the pistil. This is an exacting task requiring skilled hand labor. Natural fecundation occurs when a similar operation is carried out by birds or insects that perforate the membrane in search of food. After a few months, clusters of hanging pods (siliques) are formed; these start to yellow at the lower tip from August to September. At this point, the siliques are harvested and undergo special treatment that develops the aroma. The siliques are placed in straw baskets and dipped into hot water to rupture the inner cell wall. After a few months, the aroma starts developing. Then the siliques are exuded by intermittent exposure to sunlight (by alternately covering and uncovering the siliques with wool blankets). When exudation is complete, the siliques are oiled with cocoa oil to avoid chapping during drying and are finally dried to a suitable residual moisture content. In the final stage of the preparation, the best quality siliques form a vanilla “brine” that crystallizes on the surface of the bean. Generally, the processing of vanilla bean takes more than a year. The most important commercial qualities are brined vanilla, bastard vanilla and vanilla pompona. The bean is the only part used. Vanilla has a sweet, ethereal odor and characteristic flavor.
Chemische Eigenschaften
Vanillin has a characteristic, creamy, vanilla-like odor with a very sweet taste.
Chemische Eigenschaften
Vanillin is found in many essential oils and foods but is often not essential for their odor or aroma. However, it does determine the odor of essential oils and extracts from Vanilla planifolia and Vanilla tahitensis pods, in which it is formed during ripening by enzymatic cleavage of glycosides.
Vanillin is a colorless, crystalline solid (mp 82–83°C) with a typical vanilla odor. Because it possesses aldehyde and hydroxy substituents, it undergoes many reactions. Additional reactions are possible due to the reactivity of the aromatic nucleus. Vanillyl alcohol and 2-methoxy-4-methylphenol are obtained by catalytic hydrogenation; vanillic acid derivatives are formed after oxidation and protection of the phenolic hydroxy group. Since vanillin is a phenol aldehyde, it is stable to autoxidation and does not undergo the Cannizzaro reaction. Numerous derivatives can be prepared by etherification or esterification of the hydroxy group and by aldol condensation at the aldehyde group. Several of these derivatives are intermediates, for example, in the synthesis of pharmaceuticals.
Vanillin occurs widely in nature; it has been reported in the essential oil of Java citronella (Cymbopogon nardus Rendl.), in benzoin, Peru balsam, clove bud oil and chiefly vanilla pods (Vanilla planifolia, V. tahitensis, V. pompona); more that 40 vanilla varieties are cultivated; vanillin is also present in the plants as glucose and vanillin. Reported found in guava, feyoa fruit, many berries, asparagus, chive, cinnamon, ginger, Scotch spearmint oil, nutmeg, crisp and rye bread, butter, milk, lean and fatty fish, cured pork, beer, cognac, whiskies, sherry, grape wines, rum, cocoa, coffee, tea, roast barley, popcorn, oatmeal, cloudberry, passion fruit, beans, tamarind, dill herb and seed, sake, corn oil, malt, wort, elderberry, loquat, Bourbon and Tahiti vanilla and chicory root.
Vanillin is a flavorant made from synthetic or artificial vanilla which can be derived from lignin of whey sulfite liquors and is syntheti- cally processed from guaiacol and eugenol. the related product, ethyl vanillin, has three and one-half times the flavoring power of vanillin. vanillin also refers to the primary flavor ingredient in vanilla, which is obtained by extraction from the vanilla bean. vanillin is used as a substitute for vanilla extract, with application in ice cream, desserts, baked goods, and beverages at 60–220 ppm.
The primary component of Vanilla bean extract.
Labelled Vanillin. Occurs naturally in a wide variety of foods and plants such as orchids; major commercial source of natural vanillin is from vanilla bean extract. Synthetically produced in-bulk fro m lignin-based byproduct of paper processes or from guaicol.
An intermediate and analytical reagent.
Pharmaceutic aid (flavor). As a flavoring agent in confectionery, beverages, foods and animal feeds. Fragance and flavor in cosmetics. Reagent for synthesis. Source of L-dopa.
ChEBI: A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively.
Vorbereitung Methode
Vanillin occurs naturally in many essential oils and particularly in the pods of Vanilla planifolia and Vanilla tahitensis. Industrially, vanillin is prepared from lignin, which is obtained from the sulfite wastes produced during paper manufacture. Lignin is treated with alkali at elevated temperature and pressure, in the presence of a catalyst, to form a complex mixture of products from which vanillin is isolated. Vanillin is then purified by successive recrystallizations.
Vanillin may also be prepared synthetically by condensation, in weak alkali, of a slight excess of guaiacol with glyoxylic acid at room temperature. The resultant alkaline solution, containing 4- hydroxy-3-methoxymandelic acid is oxidized in air, in the presence of a catalyst, and vanillin is obtained by acidification and simultaneous decarboxylation. Vanillin is then purified by successive recrystallizations.
Commercial vanillin is obtained by processing waste sulfite liquors or is synthesized from guaiacol. Preparation by oxidation of isoeugenol is of historical interest only.
1) Preparation from waste sulfite liquors: The starting material for vanillin production is the lignin present in sulfite wastes from the cellulose industry. The concentrated mother liquors are treated with alkali at elevated temperature and pressure in the presence of oxidants. The vanillin formed is separated from the by-products, particularly acetovanillone (4-hydroxy-3- methoxyacetophenone), by extraction, distillation, and crystallization. A large number of patents describe various procedures for the (mainly) continuous hydrolysis and oxidation processes, as well as for the purification steps required to obtain high-grade vanillin . Lignin is degraded either with sodium hydroxide or with calcium hydroxide solution and simultaneously oxidized in air in the presence of catalysts. When the reaction is completed, the solid wastes are removed. Vanillin is extracted from the acidified solutionwith a solvent (e.g., butanol or benzene) and reextractedwith sodium hydrogen sulfite solution. Reacidification with sulfuric acid followed by vacuum distillation yields technical-grade vanillin, which must be recrystallized several times to obtain food-grade vanillin.Water, to which some ethanol may be added, is used as the solvent in the last crystallization step.
2) Preparation from guaiacol: Severalmethods can be used to introduce an aldehyde group into an aromatic ring. Condensation of guaiacol with glyoxylic acid followed by oxidation of the resulting mandelic acid to the corresponding phenylglyoxylic acid and, finally, decarboxylation continues to be a competitive industrial process for vanillin synthesis.
a. Vanillin from guaiacol and glyoxylic acid: Currently, guaiacol is synthesized from catechol, which is mainly prepared by acid-catalyzed hydroxylation of phenol with hydrogen peroxide. In China, a guaiacol prepared from o-nitrochlorobenzene via o-anisidine is also used. Glyoxylic acid is obtained as a by-product in the synthesis of glyoxal from acetaldehyde and can also be produced by oxidation of glyoxal with nitric acid. Condensation of guaiacol with glyoxylic acid proceeds smoothly at room temperature and in weakly alkaline media. A slight excess of guaiacol is maintained to avoid formation of disubstituted products; excess guaiacol is recovered. The alkaline solution containing 4-hydroxy- 3-methoxymandelic acid is then oxidized in air in the presence of a catalyst until the calculated amount of oxygen is consumed [358]. Crude vanillin is obtained by acidification and simultaneous decarboxylation of the (4-hydroxy-3-methoxyphenyl)glyoxylic acid solution.
This process has the advantage that, under the reaction conditions, the glyoxyl radical enters the aromatic guaiacol ring almost exclusively para to the phenolic hydroxy group. Tedious separation procedures are thus avoided. b. Vanillin from guaiacol and formaldehyde: An older process that is still in use consists of the reaction of guaiacolwith formaldehyde or formaldehyde precursors such as urotropine, N,N-dimethyl-aniline, and sodium nitrite .
In addition to vanillin (approximately 3%), vanilla contains other aromatic principles: vanillin, piperonal, eugenol, glucovanillin, vanillic acid, anisic acid and anisaldehyde. Although vanillin is associated with the characteristic fragrance of the plant, the quality of vanilla bean is not associated with the vanillin content. Bourbon beans contain a high amount of vanillin compared to Mexican and Tahiti beans.
Aroma threshold values
Detection: 29 ppb to 1.6 ppm; recognition: 4 ppm
Taste threshold values
Taste characteristics at 10 ppm: sweet, typical vanilla-like, marshmallow, creamy-coumarin, caramellic with a powdery nuance.
Air & Water Reaktionen
Slowly oxidizes on exposure to air. . Slightly water soluble.
Reaktivität anzeigen
Vanillin can react violently with Br2, HClO4, potassium-tert-butoxide, (tert-chloro-benzene + NaOH), (formic acid + Tl(NO3)3). . Vanillin is an aldehyde. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction).
Flash point data for Vanillin are not available, however Vanillin is probably combustible.
Pharmazeutische Anwendungen
Vanillin is widely used as a flavor in pharmaceuticals, foods, beverages, and confectionery products, to which it imparts a characteristic taste and odor of natural vanilla. It is also used in perfumes, as an analytical reagent and as an intermediate in the synthesis of a number of pharmaceuticals, particularly methyldopa. Additionally, it has been investigated as a potential therapeutic agent in sickle cell anemia and is claimed to have some antifungal properties.
In food applications, vanillin has been investigated as a preservative.
As a pharmaceutical excipient, vanillin is used in tablets, solutions (0.01–0.02% w/v), syrups, and powders to mask the unpleasant taste and odor characteristics of certain formulations, such as caffeine tablets and polythiazide tablets. It is similarly used in film coatings to mask the taste and odor of vitamin tablets. Vanillin has also been investigated as a photostabilizer in furosemide 1% w/v injection, haloperidol 0.5% w/v injection, and thiothixene 0.2% w/v injection.
Moderately toxic by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Experimental reproductive effects. Human mutation data reported. Can react violently with Br2, HClO4, potassium-tert-butoxide, tert- chlorobenzene + NaOH, formic acid + thallium nitrate. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.
There have been few reports of adverse reactions to vanillin, although it has been speculated that cross-sensitization with other structurally similar molecules, such as benzoic acid, may occur.
Adverse reactions that have been reported include contact dermatitis and bronchospasm caused by hypersensitivity.
The WHO has allocated an estimated acceptable daily intake for vanillin of up to 10 mg/kg body-weight.
LD50 (guinea pig, IP): 1.19 g/kg
LD50 (guinea pig, oral): 1.4 g/kg
LD50 (mouse, IP): 0.48 g/kg
LD50 (rat, IP): 1.16 g/kg
LD50 (rat, oral): 1.58 g/kg
LD50 (rat, SC): 1.5 g/kg
Chemical Synthesis
From the waste (liquor) of the wood-pulp industry; vanillin is extracted with benzene after saturation of the sulfite waste liquor with CO2. Vanillin is also derived naturally through fermentation.
Vanillin oxidizes slowly in moist air and is affected by light.
Solutions of vanillin in ethanol decompose rapidly in light to give a yellow-colored, slightly bitter tasting solution of 6,6’-dihydroxy- 5,5’-dimethoxy-1,1’-biphenyl-3,3’-dicarbaldehyde. Alkaline solutions also decompose rapidly to give a brown-colored solution. However, solutions stable for several months may be produced by adding sodium metabisulfite 0.2% w/v as an antioxidant.
The bulk material should be stored in a well-closed container, protected from light, in a cool, dry place.
läuterung methode
Crystallise vanillin from water or aqueous EtOH, or by distillation in vacuo.[Beilstein 8 IV 1763.]
Incompatible with acetone, forming a brightly colored compound. A compound practically insoluble in ethanol is formed with glycerin.
Regulatory Status
GRAS listed. Included in the FDA Inactive Ingredients Database (oral solutions, suspensions, syrups, and tablets). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Vanillin Upstream-Materialien And Downstream Produkte
Trichloracetaldehyd 2-Methoxy-anilin N-Methyl-anilin 2-Methoxyphenol Phenol 1-Allyl-3,4-methylendioxybenzol Benzolsulfonsäure Trichlormethan Schwefligesure N,N-Dimethyl-anilin Eugenol Hydrogenchlorid Natriumhydroxid Xylidin Methenamin Glyoxylsure Schwefelsure Calciumdihydroxid Natriumcarbonat
Downstream Produkte
3-Hydroxy-p-anisaldehyd Citronellylformiat 5-Bromvanillin Diaveridin 3,4-Dihydroxybenzoesure (E)-4'-Hydroxy-3'-methoxycinnamsure 4-Benzyloxy-3-methoxybenzaldehyd Buttersure 3,4,5-Trimethoxybenzaldehyd 1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-dien-3,5-dion 1,2,4-Trimethoxybenzol Methyldopa Citronellylpropionat 3,4-Dihydroxy-5-methoxybenzaldehyd N-((4-Hydroxy-3-methoxyphenyl)-methyl)-8-methyl-6-nonenamid, (E)- 2,3-Dimethoxybenzaldehyd 4-Aminomethyl-2-methoxyphenolhydrochlorid Veratrumaldehyd 2-Hydroxy-m-anisaldehyd 4-(2-Aminoethyl)pyrocatechinhydrobromid Isoamylalkohol 5-(2-Aminoethyl)guajakolhydrochlorid
Vanillin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.      Global( 514)Lieferanten     
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Henan Xiangtong Chemical Co., Ltd.
86-371-61312303 CHINA 153 58
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 China 19919 60
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259 CHINA 3203 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817 CHINA 21922 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693 CHINA 20680 55
Mainchem Co., Ltd.
+86-0592-6210733 CHINA 32457 55
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 CHINA 24196 60
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763 China 1751 55
Xiamen AmoyChem Co., Ltd
+86 (0)592-605 1114 CHINA 6374 58
Yancheng Green Chemicals Co.,Ltd
86-515-87883661 CHINA 349 58
121-33-5(Vanillin)Verwandte Suche:
Zimtaldehyd 2-Ethyl-3-hydroxy-4H-pyran-4-on 3,4,5-Triethoxybenzoesure 2,3,4-Trimethoxybenzaldehyd 6-Brom-3,4-dimethoxybenzaldehyd Vanillinsure 2,4,5-Trimethoxybenzoesure Veratroylchlorid 2-Hydroxy-m-anisaldehyd 3-Hydroxybenzaldehyd 2,3,4-Trihydroxybenzoesure Benzaldehyd 4-Hydroxy-3-methylbenzaldehyde 3-Methoxybenzaldehyd 7-Hydroxycitronellal 3-Ethoxy-4-hydroxybenzaldehyd Veratrumaldehyd (Trifluormethoxy)benzol
Vanillin cas:121-33-5 VANILLINE VANILLIC ALDEHYDE VANILLIN VANILLA VANILLINUM Vanilin VANILLIN FOOD GRADE,100%FINE MESH vamillic aldehyde VANILLIN FINE MESH VANILLIN 99% FCC VANILLIN 97+% NATURAL FCC VANILLIN 97+% FCC VANILLIN, REAGENTPLUS, 99% VANILLIN, PH EUR VANILLIN EPV(CRM STANDARD) VANILLIN USP(CRM STANDARD) VANILLIN 99+% VANILLINORGANIC STANDARD VANILLIN, (83°C) MELTING POINT STANDARD WHO(CRM STANDARD) VANILLIN, EXTRA PURE USP FCC VANILLIN MELTING POINT STANDARD (APPROXIMATELY 82°C) USP(CRM STANDARD) VANILLIN 99% (GC ) NATURAL VANILLIN 99+% FOR ANALYTICAL PURPOSE VANILLIN, USP STANDARD (COMING SOON) VanillinGr-(4-Hydroxy-3-Methoxybenzaldehyde) VanillinForSynthesis VanillinB.P.,U.S.P. VanillinGr VanillinGr99.9% SYNTHETIC VANILLIN (not natural) 5-Methoxyprotocatechuic aldehyde Vanillin, pure, 99% vanillin,4-hydroxy-3-methoxybenzaldehyde (3-Methoxy-4-hydroxyphenyl)methanone 4-Hydroxy-m-anisalde Vanillin ,98% Vanillin,4-Hydroxy-3-methoxybenzaldehyde, Vanillinum Vanillin, extra pure, Ph Eur, BP, NF Vanillin (200 mg) Vanillin Melting Point Standard (1 g) (Approximately 82 degrees) 3-Methoxy-4-hydroxybenzldehdye Vanillin Melting Point Standard (ApproxiMately 82 degrees) Vinillin Vanillin, pure, 99% 100GR Vanillin, pure, 99% 250GR 4-hydroxy-3-methoxy-benzaldehyd 4-hydroxy-3-methoxybenzaldehyde (vanillin) 4-Hydroxy-5-methoxybenzaldehyde 4-hydroxy-m-anisaldehyd 4-Hydroxy-m-anisaldehyde Benzaldehyde,4-hydroxy-3-methoxy- benzaldehyde,-hydroxy-3-methoxy- Lioxin m-Anisaldehyde, 4-hydroxy- Methylprotcatechuic aldehyde methyl-protocatechualdehyd m-Methoxy-p-hydroxybenzaldehyde
Urheberrecht 2017 © ChemicalBook. Alle Rechte vorbehalten.