Basic information
- Standard SMILES
COc1cc(C(=O)O)ccc1O- InChIKey
WKOLLVMJNQIZCI-UHFFFAOYSA-N- Molecular formula
- C8H8O4
- Average molar mass
- 168.15 g/mol
- Monoisotopic mass
- 168.04225874
Overview
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.
Names & identifiers
- Preferred name
- Vanillic Acid
- IUPAC
- 4-hydroxy-3-methoxybenzoic acid
- English name
- Vanillic acid
- Molecular formula
- C8H8O4
- Molecular weight
- 168.15
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
121-34-6- PubChem CID
- 8468
- DTXSID
DTXSID6059522- ChEMBL
CHEMBL120568- ChEBI
CHEBI:30816- UNII
- GM8Q3JM2Y8
- EC Number
- 204-466-8
- Nikkaji
- J5.337F
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 168
Experimental & physicochemical properties
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)
Physicochemical properties
- Melting point
- 208 · 208-210 °C(lit.)
- Boiling point
- 257.07 °C · 257.07°C (rough estimate)
- Density
- 1.3037 · 1.3037 (rough estimate)
- refractive index
- 1.509 · 1.5090 (estimate)
- FEMA
- 3988 · 3988 | 4-HYDROXY-3-METHOXYBENZOIC ACID
- FLAVIS Number
- 8.043 · 08.043 | Vanillic acid
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Acetonitrile (Slightly), Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly）
- pka
- 4.53 · pKa 4.53(H2O t = 25 c = 0.016–0.001) (Uncertain)
- form
- Liquid
- color
- Clear colorless to brown, may darken during storage
- Odor
- 100 % · at 100.00 %. dairy milky custard creamy powdery vanilla bean
- Odor Type
- creamy
- biological source
- synthetic
- Water Solubility
- Soluble in water, alcohol and ether.
- JECFA Number
- 959 · 959
- Merck
- 14 · 14,9931
- BRN
- 2208364 · 2208364
- Stability
- 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 DataBase Reference
- 121 · 121-34-6(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- VANILLIC ACID
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 8 Q3JM2Y8 · GM8Q3JM2Y8
- NIST Chemistry Reference
- 4 · Benzoic acid, 4-hydroxy-3-methoxy-(121-34-6)
- EPA Substance Registry System
- Vanillic acid (121-34-6)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 37 · 37/39-26-36
- WGK Germany
- 1 · 1
- RTECS
- 5300000 · YW5300000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29189090 · 29189090
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
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.
Hazard information
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%)
Safety data
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- YW5300000
- hs_code
- 29189090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 37/39-26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
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
Applications
DescriptionVanillic acid is a dihydroxybenzoic acid that can be used as a flavoring agent. As an oxidized form of vanillin, it is the intermediate product during the two-step bioconversion process from ferulic acid to vanillin. It exists in high amount in the root of Angelica sinenisis, which is a plant used in traditional Chinese medicine. It also exists in acal oil, argan oil as well as wine and vinegar. It can be used in the synthesis of the analeptic drug etamivan, modecainide, brovanexine, vanitiolide, and vanyldisulfamide. It can be manufactured through the oxidation of vanillin to the carboxylic acid.
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.
UsesVanillic 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.
UsesVanillin, a compound widely used in foods, beverages, cosmetics and drugs, has been reported to exhibit multifunctional effects such as antimutagenic, antiangiogenetic, anti-colitis, anti-sickling, an d antianalgesic effects. However, results of studies on the antioxidant activity of vanillin are not consistent.
UsesA flavoring agent.
General DescriptionVanillic acid is one of the key aromatic volatile compounds of vanilla beans.
Preparation methods
PreparationPrepared 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
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.
Related reactions
72 records
Linked notes
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