Grundinformationen
- Standard-SMILES
COc1cc(C(=O)O)ccc1O- InChIKey
WKOLLVMJNQIZCI-UHFFFAOYSA-N- Summenformel
- C8H8O4
- Durchschnittliche Molmasse
- 168,15 g/mol
- Monoisotopische Masse
- 168,04225874
Überblick
Vanillic acid is a monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. It has a role as a plant metabolite. It is a methoxybenzoic acid and a monohydroxybenzoic acid. It is a conjugate acid of a vanillate.
Namen und Bezeichner
- Bevorzugter Name
- Vanillic Acid
- IUPAC
- 4-hydroxy-3-methoxybenzoic acid
- Lokaler Name
- Vanillinsure
- Englischer Name
- Vanillic acid
- Summenformel
- C8H8O4
- Molmasse
- 168.15
Namen und Synonyme
Vanillic acid4-HYDROXY-3-METHOXYBENZOIC ACID121-34-6Acide vanilliqueBenzoic acid, 4-hydroxy-3-methoxy-3-Methoxy-4-hydroxybenzoic acidGM8Q3JM2Y8DTXSID6059522Acid, 4-Hydroxy-3-methoxybenzoicNSC-3987NSC-674322DTXCID1033668
Weitere Namen anzeigen
VAVanilic acidvanillicMagnoliosideVanillateVanilloidVallinic acid
FEMA NO. 3988CHEBI:30816Acid, Vanillic4 Hydroxy 3 methoxybenzoic Acidp Hydroxy m methoxy benzoic Acidp-Hydroxy-m-methoxy-benzoic AcidAcid, p-Hydroxy-m-methoxy-benzoicRefChem:6346
Datenbank-Bezeichner
- CAS
121-34-6- PubChem CID
- 8468
- DTXSID
DTXSID6059522- ChEMBL
CHEMBL120568- ChEBI
CHEBI:30816- UNII
- GM8Q3JM2Y8
- EC Number
- 204-466-8
- Nikkaji
- J5.337F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,4
- Polarare Oberfläche (TPSA)
- 66,8 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 168
Experimentelle und physikochemische Eigenschaften
Chemical ClassesBiological Agents -> Plant Oils and Extracts
DrugsPharmaceuticals -> Listed in ZINC15
FragrancesFragrance Ingredient (Vanillic acid) -> IFRA transparency List
LogP
1.43
1.46
Food Additives
FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Food
Flavoring AgentsEU Flavoring substances
Solubility
1.5 mg/mL at 14 °C
slightly soluble in water; soluble in organic solvents
soluble (in ethanol)
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point211.5 °C
Vapor Pressure0.0000171 [mmHg]
Physical Description
White odorless solid; [Merck Index] White to beige powder; [Acros Organics MSDS]
Solid
White to beige powder or needle; vanilla like odour
Dissociation Constants4.51 (at 25 °C)
Physikochemische Eigenschaften
- Schmelzpunkt
- 208 · 208-210 °C(lit.)
- Siedepunkt
- 257.07 °C · 257.07°C (rough estimate)
- Dichte
- 1.3037 · 1.3037 (rough estimate)
- Brechungsindex
- 1.509 · 1.5090 (estimate)
- FEMA
- 3988 · 3988 | 4-HYDROXY-3-METHOXYBENZOIC ACID
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- Acetonitrile (Slightly), Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly）
- pka
- 4.53 · pKa 4.53(H2O t = 25 c = 0.016–0.001) (Uncertain)
- Aggregatzustand
- Liquid
- Farbe
- Clear colorless to brown, may darken during storage
- Geruch (Odor)
- 100 % · at 100.00 %. dairy milky custard creamy powdery vanilla bean
- Geruchsart
- creamy
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- Soluble in water, alcohol and ether.
- JECFA Number
- 959 · 959
- Merck
- 14 · 14,9931
- BRN
- 2208364 · 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
- 1.3 · 1.30
- CAS Datenbank
- 121 · 121-34-6(CAS DataBase Reference)
- NIST chemische Informationen
- 4 · Benzoic acid, 4-hydroxy-3-methoxy-(121-34-6)
- EPA chemische Informationen
- Vanillic acid (121-34-6)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 72.4% (97 of 134) of all reports.
Warning
H315 (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.
Gefahrenhinweise
Regulatory Information
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/26471
Benzoic acid, 4-hydroxy-3-methoxy-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryCauses 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 CategoriesSkin Irrit. 2 (27.6%)
Sicherheitsdaten
- wgk
- 1
- tsca
- TSCA listed
- hs_code
- 29189090
- RTECS-Nr.
- YW5300000
- risk_code
- 36/37/38
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 37/39-26-36
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsCytoplasm
Verwendung und Herstellung
UsesUsed as flavoring agent or adjuvant; [FDA]
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationBenzoic acid, 4-hydroxy-3-methoxy-: ACTIVE
Anwendungen
OccurrenceReported 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.
VerwendenVanillic 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.
Darstellung
synthetischePrepared 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
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Ergänzende Hinweise
DefinitionChEBI: A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.
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