Vanillin

Vanillin Struktur
121-33-5
CAS-Nr.
121-33-5
Bezeichnung:
Vanillin
Englisch Name:
Vanillin
Synonyma:
4-HYDROXY-3-METHOXYBENZALDEHYDE;VANILLA;Vanilin;VANILLINE;2-Methoxy-4-formylphenol;VANILLINUM;3-METHOXY-4-HYDROXYBENZALDEHYDE;4-hydroxy-3-methoxybenzaldehyde (vanillin);3-Methoxy-4-hydroxybenzaldehyde (vanillin);VaniL
CBNumber:
CB8262475
Summenformel:
C8H8O3
Molgewicht:
152.15
MOL-Datei:
121-33-5.mol

Vanillin 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)
FEMA 
3107 | VANILLIN
Flammpunkt:
147 °C
storage temp. 
2-8°C
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℃)
Geruch (Odor)
at 100.00 %. vanilla
Geruchsart
vanilla
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.
LogP
1.17 at 25℃
CAS Datenbank
121-33-5(CAS DataBase Reference)
NIST chemische Informationen
Benzaldehyde, 4-hydroxy-3-methoxy-(121-33-5)
EPA chemische Informationen
Vanillin (121-33-5)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xi
R-Sätze: 22-36/37/38-36
S-Sätze: 26
WGK Germany  1
RTECS-Nr. YW5775000
Selbstentzündungstemperatur >400 °C
TSCA  Yes
HS Code  29124100
Giftige Stoffe Daten 121-33-5(Hazardous Substances Data)
Toxizität LD50 orally in rats, guinea pigs: 1580, 1400 mg/kg (Jenner)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P337+P313 Bei anhaltender Augenreizung: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

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.
Brennbar.
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.
Brennbar.

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.

Beschreibung

Vanillin is found in many plants, such as the tuber of Rhizoma Gastrodiae (Tian Ma), the whole herb of Equisetum (Mu Zei), Ulva pertusa (Kong Shi Chun), and sugar beets, vanilla beans, Peru balsam, and so on .

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.

Physikalische Eigenschaften

Appearance: white or light yellow needle crystal or crystal powder, with a strong aroma. The relative density is about 1.060. Solubility: It is not only soluble in ethanol, chloroform, ether, carbon disulfide, glacial acetic acid, and pyridine but also in oil, propylene glycol, and hydrogen peroxide in alkaline solution. It can slowly oxidize in the air, can be unstable under illumination, and should be stored in a dark condition. Melting point: the melting point is 81°C.

Occurrence

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.

History

Vanillin is known as one of the first synthetic spices. In the perfume industry, it is known as vanillic aldehyde. As early as 1858, French chemist Gby (NicolasTheodore Gobley) obtained pure vanillin for the first time by the method of rectification. Due to less production yield of natural vanillin, it spurred the search for a chemical synthesis method of vanillin production. In 1874, German scientist M.?Haarman and co-workers deduced the chemical structure of vanillin and discovered a new way to produce vanillin with abietene as the raw material . In 1965, Chinese scientists found that vanillin has antiepileptic effect and accomplished a study on the pharmacology and toxicology of vanillin from edible to officinal. They also found that vanillin has certain antibacterial activity, making it a suitable drug formulation for the treatment of skin disease. Vanillin can be used as intermediate for synthesis of a variety of drugs, such as berberine and antihypertensive drug L-methyldopa, methoxy-pyrimidine, and heart disease drug papaverine .

Verwenden

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.

Definition

ChEBI: A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively.

Indications

It can be used to treat various types of epilepsy and attention deficit hyperactivity disorder and vertigo.

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.

Allgemeine Beschreibung

Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards

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).

Brandgefahr

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.

Clinical Use

Vanillin tablet has been used in the treatment of epilepsy and has a better therapeutic effect. Some patients have a minor dizziness response occasionally in the clinic.

Sicherheitsprofil

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.

Sicherheit(Safety)

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

Stoffwechsel

Early observers noted conversion of vanillin to vanillic acid which was excreted mainly as the free acid, a conjugated ethereal sulphate or glucurovanillic acid (Preusse, 1880). In man, vanillin is broken down by the liver to vanillic acid which is excreted in the urine. Human liver homogenates readily convert vanillin to vanillic acid in vitro (Dirscherl & Brisse, 1966). Endogenous vanillic acid production and excretion in man from body catecholamines amounts to <0.5 mg/day, compared with the normal contribution from dietary sources of about 9 mg/day (Dirscherl & Wirtzfeldt, 1964).

Lager

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.]

Inkompatibilitäten

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

Upstream-Materialien

Downstream Produkte


Vanillin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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121-33-5(Vanillin)Verwandte Suche:


  • 4-Formyl-2-methoxyphenol
  • Protocatechualdehyde, methyl-
  • protocatechualdehyde3-methylether
  • p-Vanillin
  • Vanillaldehyde
  • vanillin (3-methoxy-4-hydroxy- benzaldehyde)
  • Zimco
  • METHYL PROTOCATECHUIC ALDEHYDE
  • LABOTEST-BB LT00429580
  • METHOXYPROTOCATECHUIC ALDEHYDE
  • AURORA 4274
  • AKOS BBS-00003189
  • OTAVA-BB BB0109160039
  • Methyl vanillin (3-Methoxy-4-hydroxybenzaldehyde)
  • VANILLIN,NF
  • PARA-VANILLIN
  • VANILLIN CHEM. REIN 100 P. DAB 8
  • VANILLIN AKA 4-HYDROXY-3-METHOXY BENZALDEHYDE
  • VANILLIN WITH GC
  • 4-Hydroxy-3-methoxybenzaldehyde( Vanilline)
  • Vanillin (contains H2SO4) Ethanol Solution [for TLC Stain]
  • VANILLIN USP FROM EUGENOL
  • VANILLIN, NATURAL EX-CLOVE
  • VANILLIN, NATURAL EX-EUGENOL
  • VANILLIN, NATURAL EX-TUMERIC
  • VANILLIN, NATURAL EX-VANILLA
  • VANILIN extrapure AR,
  • Vanillin, typically 99%
  • Vanillin, AR,99%
  • Vanilla pods extract
  • Vanillin ReagentPlus(R), 99%
  • Vanillin Vetec(TM) reagent grade, 98%
  • Mettler-Toledo Calibration substance ME 51143093, Vanillin
  • VANILLIN
  • 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)
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