4-Hydroxy-3-methoxyphenylacetic Acid - 10mM in DMSO , CAS No.306-08-1

CAS: 306-08-1 Cat. No.: H423170 Molecular Weight: 182.18 Beilstein Registry Number: 10409 EC Number: 206-176-7

GRADE & PURITY 10mM in DMSO

Synonyms

HMS2233B24 | UNII-X77S6GMS36 | HMDB00118 | NCGC00093999-02 | SMR000326729 | HMS3261P06 | homovanillic-acid | MLS001056771 | 4-HYDROXY-3-METHOXYPHENYLACETIC ACID (2,5,6-D3,ALPHA,ALPHA-D2) | Acetic acid, (4-hydroxy-3-methoxyphenyl)- | Acetic acid, (4-hydrox

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Homovanillic acid has been used as a standard in HPLC analysis.

Specifications

Synonyms

HMS2233B24 | UNII-X77S6GMS36 | HMDB00118 | NCGC00093999-02 | SMR000326729 | HMS3261P06 | homovanillic-acid | MLS001056771 | 4-HYDROXY-3-METHOXYPHENYLACETIC ACID (2, 5, 6-D3, ALPHA, ALPHA-D2) | Acetic acid, (4-hydroxy-3-methoxyphenyl)- | Acetic acid, (4-hydrox

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Fluorimetric reagent and major catecholamine metabolite. Used for fluorimetric determination of oxidative enzymes including glucose oxidase.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: COC1=C(C=CC(=C1)CC(=O)O)O
• IUPAC Name: 2-(4-hydroxy-3-methoxyphenyl)acetic acid
• InChIKey: QRMZSPFSDQBLIX-UHFFFAOYSA-N
• INCHI: 1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
• Isomeric SMILES: COC1=C(C=CC(=C1)CC(=O)O)O
• Molecular Weight: 182.18
• Beilstein: 10409
• Reaxy-Rn: 2213447
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2213447&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenols
      • Subclass Methoxyphenols

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenols
• Subclass: Methoxyphenols
• Intermediate Tree Nodes: Not available
• Direct Parent: Methoxyphenols
• Alternative Parents: Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Methoxyphenol - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Ether - Carboxylic acid - Organic oxygen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
• External Descriptors: monocarboxylic acid - phenols - monomethoxybenzene

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)

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

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

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

Discover Target: TSHR

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

CSNK2A1 Tchem Casein kinase II alpha (3512 Activities)

Discover Target: CSNK2A1

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

ARSA Tbio Cerebroside-sulfatase (655 Activities)

Discover Target: ARSA

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

GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)

Discover Target: GAA

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

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

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

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

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

NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

Discover Target: NFKB1

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

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

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

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

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

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

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

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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

U-937 (7138 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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

SLC22A8 Tclin Solute carrier family 22 member 8 (241 Activities)

Discover Target: SLC22A8

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

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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

ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

Discover Target: ATAD5

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

MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)

Discover Target: MPHOSPH8

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UGT1A6 Tbio UDP-glucuronosyltransferase 1-6 (221 Activities)

Discover Target: UGT1A6

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UGT1A9 Tbio UDP-glucuronosyltransferase 1-9 (343 Activities)

Discover Target: UGT1A9

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

RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

Discover Target: RGS4

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

pfk 6-phospho-1-fructokinase (7870 Activities)

Discover Target: pfk

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

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clpP ATP-dependent Clp protease proteolytic subunit (245 Activities)

Discover Target: clpP

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light and air sensitive
• Melt Point(°C): 140-145℃
• Molecular Weight: 182.170 g/mol
• XLogP3: 0.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.058 Da
• Monoisotopic Mass: 182.058 Da
• Topological Polar Surface Area: 66.800 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. Xin Huang, Rui Wang, Yikai Wang, Changbao Chen, Shuying Liu.  (2022)  Investigation on property differences of ginseng and American ginseng by spatial metabolomics of neurochemicals with desorption electrospray ionization mass spectrometry imaging.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:36516905] [10.1016/j.jep.2022.116006]

2. Jindong Wang, Wenzhi Li, Huizhen Wang, Ajibola Temitope Ogunbiyi, Xiaomeng Dou, Qiaozhi Ma.  (2020)  Effects of the novel catalyst Ni–S2O82−–K2O/TiO2 on efficient lignin depolymerization.  RSC Advances,  10  (14): (8558-8567).  [PMID:35497830] [10.1039/C9RA10675H]

3. Chen Li, Xuejuan Chen, Zhe Zhang, Jilin Tang, Bailin Zhang.  (2018)  Gold Nanoparticle-DNA conjugates enhanced determination of dopamine by aptamer-based microcantilever array sensor.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2018.08.024]

4. Kuangyi Zou, Qianming Li, Dan Li, Yiding Jiao, Lie Wang, Luhe Li, Jiacheng Wang, Yiran Li, Rui Gao, Fangyan Li, Er He, Tingting Ye, Wentao Tang, Jie Song, Jiang Lu, Xusong Li, Hanting Zhang, Xinyin Cao, Ye Zhang.  (2024)  A Highly Selective Implantable Electrochemical Fiber Sensor for Real-Time Monitoring of Blood Homovanillic Acid.  ACS Nano,      [PMID:38415599] [10.1021/acsnano.3c11641]

5. Zhiyu Zhang, Cheng Yang, Di Zhao, Yuanqing Zhao, Lixin Li, Zhonghua Li, Zhenqiang Zhang, Kai Hu.  (2024)  Boric Acid Functionalized Hypercrosslinked Polymers for Selective Extraction of Trace Catecholamines and Their Metabolites in Rat Serum.  JOURNAL OF SEPARATION SCIENCE,  47  (18): (e202400418).  [PMID:39304642] [10.1002/jssc.202400418]

6. Kai Li, Yuan Wang, Xiao Guo, Bo Wang.  (2024)  Effects of Lignin-Diverted Reductant with Polyphenol Oxidases on Cellulose Degradation by Wild and Mutant Types of Lytic Polysaccharide Monooxygenase.  CURRENT ISSUES IN MOLECULAR BIOLOGY,  46  (4): (3694-3712).  [PMID:38666960] [10.3390/cimb46040230]

7. Xuezhi Shao, Hongliang Fang, Tao Li, Liyan Yang, Dengfeng Yang, Lixia Pan.  (2024)  Heterologous Expression and Biochemical Characterization of a Novel Lytic Polysaccharide Monooxygenase from Chitinilyticum aquatile CSC-1.  Microorganisms,  12  (7): (1381).  [PMID:39065150] [10.3390/microorganisms12071381]

8. Hui Dong, Zuying Wang, Aixin Chang, Miaomiao Zhao, Siyu Wang, Yifan Li, Chenxi Su, Jiaxin Zhou, Zhiqin Zhang, Yanli Zhou, Zhaohui Li, Maotian Xu.  (2025)  A ratiometric electrochemical sensor based on molecular imprinting for highly selective detection of HVA.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.114931]

9. Lu Li, Xiaodi Liu, Shijie Xu, Shiming Zhang, Zhuangzhuang Yang, Debao Xiao.  (2025)  Electrochromic platform for the visual detection of the neuroblastoma biomarkers vanillylmandelic acid and homovanillic acid.  ANALYST,      [PMID:40223690] [10.1039/D5AN00228A]