Vanillic acid

Iupac Name：4-hydroxy-3-methoxybenzoic acid

Molecular Weight：168.14672

Modify Date.: 2022-11-29 12:18

Introduction: Vanillic 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. View more+

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1. Names and Identifiers

1.1 Name: Vanillic acid
1.2 Synonyms: 2-Methoxy-4-carboxyphenol 3-Methoxy-4-hydroxybenzoic acid 4-Carboxyl-2-methoxyphenol 4-HYDROXY-3-METHOXYBENZOIC ACID 4-Hydroxy-3-methoxy-benzoic acid 4-hydroxy-m-Anisic acid Acid, Vanillic AKOS BBS-00003785 Benzoic acid, 4-hydroxy-3-methoxy- EINECS 204-466-8 FEMA 3988 Methylprotocatechuic acid MFCD00002551 m-Methoxy-p-hydroxy-benzoic acid NSC 3987 NSC 674322 PROTOCATECHUIC ACID 3-METHYL ETHER RARECHEM AL BO 0061 TIMTEC-BB SBB008280 VA VENILLIC ACID

1.3 CAS No.: 121-34-6

1.4 CID: 8468

1.5 EINECS(EC#): 204-466-8

1.6 Molecular Formula: C8H8O4 (isomer)

1.7 Inchi: InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)

1.8 InChkey: WKOLLVMJNQIZCI-UHFFFAOYSA-N

1.9 Canonical Smiles: COC1=C(C=CC(=C1)C(=O)O)O

1.10 Isomers Smiles: COC1=C(C=CC(=C1)C(=O)O)O

2. Properties

2.1 Density: 1.351

2.1 Melting point: 209-213℃

2.1 Boiling point: 353.4 oC at 760 mmHg

2.1 Refractive index: 1.5090 (estimate)

2.1 Flash Point: 149.4 oC

2.1 Precise Quality: 168.04200

2.1 PSA: 66.76000

2.1 logP: 1.09900

2.1 Appearance: Solid

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: white odourless crystals or powder

2.4 Color/Form: Powder

2.5 pKa: pKa 4.53(H2Ot = 25c = 0.016–0.001) (Uncertain)

2.6 Water Solubility: 1.5 mg/mL at 14 °C

2.7 Stability: Stable. Combustible. Incompatible with strong oxidizing agents.

2.8 StorageTemp: Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

3. Use and Manufacturing

3.1 Definition: ChEBI: A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.

3.2 Usage: Vanillin, 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, and antianalgesic effects. However, results of studies on the antioxidant activity of vanillin are not consistent.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Declaration: H315

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 1

4.1 RTECS: YW5300000

4.1 Report: Reported in EPA TSCA Inventory.

4.2 Safety: Safety Information of Vanillic acid (CAS NO.121-34-6):
Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 37/39-26-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.?
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 1
RTECS: YW5300000
Hazard Note: Irritant
Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

4.3 Specification: ?Vanillic acid (CAS NO.121-34-6), its Synonyms are 3-Methoxy-4-hydroxybenzoic acid ; 4-Hydroxy-3-methoxybenzoic acid ; Benzoic acid, 4-hydroxy-3-methoxy- ; Acide vanillique ; Protocatechuic acid, 3-methyl ester ; VA ; m-Anisic acid, 4-hydroxy- ; p-Vanillic acid .

4.4 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	> 2691mg/kg (2691mg/kg)	?	Yakugaku Zasshi. Journal of Pharmacy. Vol. 104, Pg. 793, 1984.
rat	LD50	intraperitoneal	5020mg/kg (5020mg/kg)	?	Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 243, Pg. 609, 1956.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

121-34-6Total: 20 Synthesis Route

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121-34-6 212 Suppliers

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121-33-5 638 Suppliers

Literatures:
Unno, Tatsuya; Kim, Soo-Jin; Kanaly, Robert A.; Ahn, Joong-Hoon; Kang, Su-Il; Hur, Hor-Gil Journal of Agricultural and Food Chemistry, 2007 , vol. 55, # 21 p. 8556 - 8561
Yield: null

93-51-6 126 Suppliers

498-00-0 97 Suppliers

121-34-6 212 Suppliers

5533-03-9 2 Suppliers

Literatures:
Jiang, Qing; Sheng, Wenbing; Guo, Xiangdong; Tang, Jie; Guo, Cancheng Journal of Molecular Catalysis A: Chemical, 2013 , vol. 373, p. 121 - 126
Yield: null

97-54-1 98 Suppliers

2034-61-9

4899-73-4

121-34-6 212 Suppliers

Literatures:
Kraus, Rupert; Spiteller, Gerhard Phytochemistry (Elsevier), 1990 , vol. 29, # 5 p. 1653 - 1659
Yield: null

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8. Other Information

8.0 Usage: 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.

8.1 Collision Cross Section: 136.2 ?2 [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

8.2 Mesh Entry Terms: 4 Hydroxy 3 methoxybenzoic Acid

8.3 Manufacturing Info: Benzoic acid, 4-hydroxy-3-methoxy-: ACTIVE

8.4 Use Classification: Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index

9. Computational chemical data

Molecular Weight: 168.14672g/mol
Molecular Formula: C₈H₈O₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 168.04225873
Monoisotopic Mass: 168.04225873
Complexity: 168
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 66.8
Heavy Atom Count: 12
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADASAmAIyDoAABgCIAiDSCAACCAAkIAAIiAEGiMgNJjKGNRqAcSMkwBELuYfK7DTOIAABAAAAQABAAAIAAACAAAAAAAAAAA==

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