Methyl Vanillate - ≥99% , CAS No.3943-74-6

CAS: 3943-74-6 Cat. No.: M102757 Molecular Weight: 182.17 Beilstein Registry Number: 10(3)1410 EC Number: 223-525-9

GRADE & PURITY ≥99%

Synonyms

3-methoxy-4-(hydroxy)benzoic acid methyl ester | 4-hydroxy-5-methoxy-benzoic acid methyl ester | AKOS000120673 | Methyl 4-hydroxy-3-methoxybenzoate | methyl 4-hydroxy-3-methoxy-benzoate | BENZOIC ACID, 4-HYDROXY-3-METHOXY-, METHYL ESTER | Q27097897 | 4-Hy

Storage

Room temperature

Shipped In

Normal

Overview

Methyl vanillate is a volatile compound present in cloudberries (Rubus Chamaemorus.).

Specifications

Synonyms

3-methoxy-4-(hydroxy)benzoic acid methyl ester | 4-hydroxy-5-methoxy-benzoic acid methyl ester | AKOS000120673 | Methyl 4-hydroxy-3-methoxybenzoate | methyl 4-hydroxy-3-methoxy-benzoate | BENZOIC ACID, 4-HYDROXY-3-METHOXY-, METHYL ESTER | Q27097897 | 4-Hy

Specifications & Purity

≥99%

Storage

Room temperature

Shipped In

Normal

Action Type

ACTIVATOR

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488182566
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488182566
• Canonical Smiles: COC1=C(C=CC(=C1)C(=O)OC)O
• IUPAC Name: methyl 4-hydroxy-3-methoxybenzoate
• InChIKey: BVWTXUYLKBHMOX-UHFFFAOYSA-N
• INCHI: 1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3
• Isomeric SMILES: COC1=C(C=CC(=C1)C(=O)OC)O
• WGK Germany: 3
• RTECS: DH2430000
• Molecular Weight: 182.17
• Beilstein: 10(3)1410
• Reaxy-Rn: 1369113
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1369113&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Level5 Methoxybenzoic acids and derivatives
          • Level6 M-methoxybenzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Methoxybenzoic acids and derivatives
• Direct Parent: M-methoxybenzoic acids and derivatives
• Alternative Parents: p-Hydroxybenzoic acid alkyl esters Methoxyphenols Phenoxy compounds Methoxybenzenes Benzoyl derivatives Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Methyl esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: P-hydroxybenzoic acid alkyl ester - P-hydroxybenzoic acid ester - M-methoxybenzoic acid or derivatives - Methoxyphenol - Benzoate ester - Phenoxy compound - Anisole - Methoxybenzene - Benzoyl - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Methyl ester - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Ether - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
• External Descriptors: aromatic ether - phenols - benzoate ester

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

LoVo (4724 Activities)

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MCF7 (126967 Activities)

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PC-3 (62116 Activities)

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T98G (1524 Activities)

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A549 (127892 Activities)

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OE33 (225 Activities)

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Associated Targets(non-human)

Ralstonia solanacearum (520 Activities)

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Agrobacterium tumefaciens (620 Activities)

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Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Salmonella enteritidis (727 Activities)

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Bacillus cereus (7522 Activities)

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Candida albicans (78123 Activities)

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RBL-2H3 (1162 Activities)

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B16-F10 (4610 Activities)

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Pseudomonas tolaasii (36 Activities)

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Trichophyton mentagrophytes (4846 Activities)

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PPO Polyphenol oxidase (10 Activities)

Discover Target: PPO

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in chloroform and methanol.
• Boil Point(°C): 285-287°C
• Melt Point(°C): 64-67°C
• Molecular Weight: 182.170 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.058 Da
• Monoisotopic Mass: 182.058 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 180.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Weibo Zhang, Chong Chen, Yixuan Li, Fengyu Guo, Weiqian Liu, Siyuan Liu, Yanan sun, Xifan Wang, Yuemin Shen, Pengjie Wang.  (2023)  Analysis of composition and source of the key aroma compounds in stir-fried pepper tallow.  FOOD CHEMISTRY,      [PMID:38218145] [10.1016/j.foodchem.2023.138321]

2. Jian Yao, Lun Gui, Qizhang Long.  (2022)  A chlorogenic acid esterase from a metagenomic library with unique substrate specificity and its application in caffeic and ferulic acid production from agricultural byproducts.  BIOCATALYSIS AND BIOTRANSFORMATION,      [PMID:] [10.1080/10242422.2021.1969370]

3. Yao Jian, Gui Lun, Yin Shaocheng.  (2021)  A novel esterase from a soil metagenomic library displaying a broad substrate range.  AMB Express,  11  (1): (1-10).  [PMID:33666762] [10.1186/s13568-021-01198-5]

4. Li Shuo, Xu Tongan, Deng Ming, Jia Ruyan, Djouonkep Lesly Dasilva Wandji.  (2025)  Structure–Property Relationships of Renewable Ternary Polyesters Derived from Vanillin-Based Methyl Ester, Aliphatic Diacids, and Phenol Ether-Based Diols.  JOURNAL OF POLYMERS AND THE ENVIRONMENT,      [PMID:] [10.1007/s10924-025-03643-z]

5. Weisheng Yang, Liang Jiao, Xiu Wang, Weibing Wu, Hailan Lian, Hongqi Dai.  (2020)  Formaldehyde-free self-polymerization of lignin-derived monomers for synthesis of renewable phenolic resin.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:33161075] [10.1016/j.ijbiomac.2020.11.012]

6. Tianyin Huang, Yifan Yu, Wentao Zhang, Yue Zhao, Yiliang Tao, Wenguang Huang, Bingdang Wu.  (2026)  Molecular orbital-guided design of laccase–mediator systems for antibiotic removal in the presence of humic acid.  BIORESOURCE TECHNOLOGY,      [PMID:41513177] [10.1016/j.biortech.2026.133957]