Isovanillic acid - ≥97% , CAS No.645-08-9

CAS: 645-08-9 Cat. No.: I113428 Molecular Weight: 168.15 Beilstein Registry Number: 10393 EC Number: 211-430-5

GRADE & PURITY ≥97%

Synonyms

DTXSID40214745 | CCG-266344 | EINECS 211-430-5 | GS-3245 | 3-Hydroxy-p-anisic acid | UNII-A8D1DUX2PR | AC-2478 | 3-Hydroxyanisic acid | Acide isovanillique | InChI=1/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11 | SCHEMBL180473 | Benzoic acid,

Storage

Room temperature

Shipped In

Normal

Overview

It can be used in the synthesis of opiate alkaloid precursor, dihydrothebainone.

Specifications

Synonyms

DTXSID40214745 | CCG-266344 | EINECS 211-430-5 | GS-3245 | 3-Hydroxy-p-anisic acid | UNII-A8D1DUX2PR | AC-2478 | 3-Hydroxyanisic acid | Acide isovanillique | InChI=1/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4, 9H, 1H3, (H, 10, 11 | SCHEMBL180473 | Benzoic acid,

Specifications & Purity

≥97%

Storage

Room temperature

Shipped In

Normal

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 488181703
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488181703
• Canonical Smiles: COC1=C(C=C(C=C1)C(=O)O)O
• IUPAC Name: 3-hydroxy-4-methoxybenzoic acid
• InChIKey: LBKFGYZQBSGRHY-UHFFFAOYSA-N
• INCHI: 1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)
• Isomeric SMILES: COC1=C(C=C(C=C1)C(=O)O)O
• WGK Germany: 3
• RTECS: BZ4850000
• Molecular Weight: 168.15
• Beilstein: 10393
• Reaxy-Rn: 2208365
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2208365&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 P-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: P-methoxybenzoic acids and derivatives
• Alternative Parents: Methoxyphenols Hydroxybenzoic acid derivatives Benzoic acids Phenoxy compounds Methoxybenzenes Benzoyl derivatives Anisoles Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: P-methoxybenzoic acid or derivatives - Hydroxybenzoic acid - Methoxyphenol - Benzoic acid - Phenoxy compound - Benzoyl - Phenol ether - Methoxybenzene - Anisole - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Alkyl aryl ether - 1-hydroxy-4-unsubstituted benzenoid - Carboxylic acid - Monocarboxylic acid or derivatives - Ether - Carboxylic acid derivative - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.
• External Descriptors: monohydroxybenzoic acid - methoxybenzoic acid

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)

TYR Tclin Tyrosinase (717 Activities)

Discover Target: TYR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

COMT Tclin Catechol O-methyltransferase (404 Activities)

Discover Target: COMT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TPMT Tchem Thiopurine S-methyltransferase (45 Activities)

Discover Target: TPMT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

PPO Polyphenol oxidase (10 Activities)

Discover Target: PPO

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 250-253°C
• Molecular Weight: 168.150 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.042 Da
• Monoisotopic Mass: 168.042 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 168.000
• 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. Bo Chen, Jie Zhou, Qilu Meng, Yang Zhang, Shihua Zhang, Liang Zhang.  (2018)  Comparative analysis of fecal phenolic content between normal and obese rats after oral administration of tea polyphenols.  Food & Function,  9  (9): (4858-4864).  [PMID:30156246] [10.1039/C8FO00609A]

2. Yuandong Yu, Guizhao Liang.  (2021)  Interaction mechanism of phenolic acids and zein: A spectrofluorometric and molecular dynamics investigation.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2021.118032]

3. He Wang, Yanjing Guo, Yu Ji, Qing Liu, Qizhen Chen, Qianlong Zhang, Mingying Yang, Bernal E. Valverde, Shiguo Chen.  (2025)  Herbicidal mechanism of Isovanillic acid and computational structure-guided design of high-potency derivatives.  PEST MANAGEMENT SCIENCE,      [PMID:41414656] [10.1002/ps.70469]