3,4-Methylenedioxycinnamic Acid - ≥99% , CAS No.2373-80-0

CAS: 2373-80-0 Cat. No.: M124601 Molecular Weight: 192.17 Beilstein Registry Number: 19278 EC Number: 219-151-0

GRADE & PURITY ≥99%

Synonyms

BBL012089 | Z56789057 | (e)-3-benzo[1,3]dioxol-5-yl-acrylic acid | 3,4-Methylenedioxybenzene-3-acrylic acid | BDBM50486070 | InChI=1/C10H8O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1-5H,6H2,(H,11,12)/b4-2 | 3,4-methylendioxycinnamic acid | HMS1397A21 | pip

Storage

Room temperature

Shipped In

Normal

Overview

3,4-(Methylenedioxy)cinnamic acid is an inhibitor of the phenylpropanoid enzyme 4-hydroxycinnamoyl-CoA ligase. It undergoes electron transfer reaction with trichloromethylperoxyl radical and reaction has been studied by pulse radiolysis.
An inhibitor of the phenylpropanoid enzyme 4-hydroxycinnamoyl-CoA ligase.

Specifications

Synonyms

BBL012089 | Z56789057 | (e)-3-benzo[1, 3]dioxol-5-yl-acrylic acid | 3, 4-Methylenedioxybenzene-3-acrylic acid | BDBM50486070 | InChI=1/C10H8O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1-5H, 6H2, (H, 11, 12)/b4-2 | 3, 4-methylendioxycinnamic acid | HMS1397A21 | pip

Specifications & Purity

≥99%

Storage

Room temperature

Shipped In

Normal

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488190951
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488190951
• Canonical Smiles: C1OC2=C(O1)C=C(C=C2)C=CC(=O)O
• IUPAC Name: (E)-3-(1,3-benzodioxol-5-yl)prop-2-enoic acid
• InChIKey: QFQYZMGOKIROEC-DUXPYHPUSA-N
• INCHI: 1S/C10H8O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1-5H,6H2,(H,11,12)/b4-2+
• Isomeric SMILES: C1OC2=C(O1)C=C(C=C2)/C=C/C(=O)O
• WGK Germany: 3
• Molecular Weight: 192.17
• Beilstein: 19278
• Reaxy-Rn: 84599
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=84599&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Cinnamic acids and derivatives
      • Subclass Hydroxycinnamic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Cinnamic acids and derivatives
• Subclass: Hydroxycinnamic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumaric acids and derivatives
• Alternative Parents: Benzodioxoles Styrenes Oxacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Acetals Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumaric acid or derivatives - Benzodioxole - Styrene - Benzenoid - Acetal - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organic oxide - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
• External Descriptors: hydroxycinnamic 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)

FEN1 Tchem Flap endonuclease 1 (12055 Activities)

Discover Target: FEN1

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VCP Tchem Transitional endoplasmic reticulum ATPase (895 Activities)

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Associated Targets(non-human)

NA Neuraminidase (1107 Activities)

Discover Target: NA

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Hcar2 Hydroxycarboxylic acid receptor 2 (55 Activities)

Discover Target: Hcar2

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Mycobacterium tuberculosis (203094 Activities)

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Mycolicibacterium smegmatis (8003 Activities)

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Hepatitis B virus (7925 Activities)

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Influenza A virus (11224 Activities)

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MDCK (10148 Activities)

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RAW264.7 (28094 Activities)

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Mycobacterium tuberculosis variant bovis BCG (1626 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 242-244°C
• Molecular Weight: 192.170 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 192.042 Da
• Monoisotopic Mass: 192.042 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 249.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Hujun Niu, Xudong Chen, Yunbo Zhao, Junyi Zhou, Yimin Xie.  (2023)  Exploration of the Linkages between Lignin and Carbohydrates in Kraft Pulp from Wheat Straw Using a 13C/2H Isotopic Tracer.  MOLECULES,  28  (22): (7493).  [PMID:38005215] [10.3390/molecules28227493]

2. Yupei Sun, Yanhui Yi, Bingkang Wang, Jinrong Li, Feng Zhao, Jianzeng Xin, Sheng Liu.  (2026)  Design, synthesis and anti-tumor activation of β-carboline alkaloids derivatives from Picrasma quassioides.  FITOTERAPIA,      [PMID:] [10.1016/j.fitote.2026.107209]