HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Vanillinsure
VA · 4-HYDROXY-3-METHOXYBENZOIC ACID · Benzoic acid, 4-hydroxy-3-methoxy- · Vanilic acid · vanillic · 3-Methoxy-4-Hydroxybenzoic acid · Magnolioside · Vanillate
Identifikatoren & physikalische Daten
| CAS No. | 121-34-6 |
|---|---|
| Summenformel | C8H8O4 |
| Durchschnittliche Molmasse | 168,15 g/mol |
| Monoisotopische Masse | 168,04225874 g/mol |
| SMILES | COc1cc(C(=O)O)ccc1O |
| InChIKey | WKOLLVMJNQIZCI-UHFFFAOYSA-N |
| PubChem CID | 8468 |
| ChEMBL | CHEMBL120568 |
| ChEBI | CHEBI:30816 |
| EC No. | 204-466-8 |
| DTXSID | DTXSID6059522 |
| Lokaler Name | Vanillinsure |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 66,8 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 168 |
| Stoffklassen | Biological Agents -> Plant Oils and Extracts |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Duftstoffe | Fragrance Ingredient (Vanillic acid) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | 1.431.46 |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | 1.5 mg/mL at 14 °Cslightly soluble in watersoluble in organic solventssoluble (in ethanol)Acetonitrile (Slightly), Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly）Soluble in water, alcohol and ether. |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 211.5 °C208-210 °C(lit.) |
| Dampfdruck | 0.0000171 [mmHg] |
| Physical Description | White odorless solid[Merck Index] White to beige powder[Acros Organics MSDS]White to beige powder or needlevanilla like odour |
| Dissociation Constants | 4.51 (at 25 °C) |
| Siedepunkt | 257.07°C (rough estimate) |
| Dichte | 1.3037 (rough estimate) |
| Brechungsindex | 1.5090 (estimate) |
| FEMA | 3988 | 4-HYDROXY-3-METHOXYBENZOIC ACID |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | pKa 4.53(H2O t = 25 c = 0.016–0.001) (Uncertain) |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to brown, may darken during storage |
| Geruch | at 100.00 %. dairy milky custard creamy powdery vanilla bean |
| Geruchsart | creamy |
| Biologische Quelle | synthetic |
| JECFA Number | 959 |
| Merck | 14,9931 |
| BRN | 2208364 |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) |
| InChIKey | WKOLLVMJNQIZCI-UHFFFAOYSA-N |
| SMILES | COc1cc(ccc1O)C(O)=O |
| LogP (Verteilungskoeffizient) | 1.30 |
| CAS Datenbank | 121-34-6(CAS DataBase Reference) |
| NIST chemische Informationen | Benzoic acid, 4-hydroxy-3-methoxy-(121-34-6) |
| EPA chemische Informationen | Vanillic acid (121-34-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 72.4% (97 of 134) of all reports.WarningH315 (27.6%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 134 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzoic acid, 4-hydroxy-3-methoxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 10-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/26471Benzoic acid, 4-hydroxy-3-methoxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | Causes other liver changes, effects on other transferases, and inflammatory effects in acute intraperitoneal studies of mice[RTECS] Safe when used as a flavoring agent in food[JECFA] An irritant[Acros Organics MSDS] See Vanillin. |
| Hazard Classes and Categories | Skin Irrit. 2 (27.6%) |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29189090 |
| RTECS-Nr. | YW5300000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 37/39-26-36 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Occurrence
Reported found in guava, grape, brandy, rum, whiskey, sherry, red and white wines, Scotch and Canadian whiskey, pork (fried), cocoa, peanuts (raw), mushrooms, guava fruit, mangos (fresh), wort, vanilla and black chokeberries.
Verwenden
Vanillic acid is used as a flavoring agent in food. It acts as an intermediate in the production of vanillin from ferulic acid. Further, it is used in wine and vinegar.
Herstellung & Synthese
synthetische
Prepared by bioconversion of ferulic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BS13. Also prepared by whole-cell bioconversion of vanillin to vanillic acid by Streptomyces viridosporus