A phenol with diverse biological activities
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Isomer(s)
364272-Methoxy-4-vinylphenol
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4-Allylcatechol

Item No. 36542

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(2-propen-1-yl)-1,2-benzenediol
CAS Number
1126-61-0
Synonyms
  • Hydroxychavicol
  • 4-Allylbenzene-1,2-diol
  • 4‑Allylpyrocatechol
  • 1,2-Dihydroxy-4-allylbenzene
Molecular Formula
C9H10O2
Formula Weight
150.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
OC1=CC=C(CC=C)C=C1O
InChi Code
InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2
InChi Key
FHEHIXJLCWUPCZ-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $55

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    10 mg

    $99

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    50 mg

    $440

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    100 mg

    $770

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    Cayman Chemical
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    Product Description

    4-Allylcatechol is a phenol that has been found in P. betle and has diverse biological activities.1,2,3,4 It scavenges DPPH (Item No. 14805) radicals, reduces the formation of thiobarbituric acid reactive substances (TBARS), and inhibits xanthine oxidase in cell-free assays (IC50s = 20.17, 2, and 16.7 µM, respectively).1,2 4-Allylcatechol is cytotoxic to HT-29 colon cancer cells (IC50 = 30 µg/ml).3 It reduces paw edema and arthritic paw tissue homogenate levels of IL-1β, prostaglandin E2 (PGE2; Item No. 14010), leukotriene B4 (LTB4; Item No. 20110), and nitric oxide (NO) in a mouse model of steam-killed M. tuberculosis-induced arthritis when administered at a dose of 4 mg/kg.4 4-Allylcatechol has been used as a precursor in the synthesis of, and is a metabolite of, safrole.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rathee, J.S., Patro, B.S., Mula, S., et al. Antioxidant activity of Piper betel leaf extract and its constituents. J. Agric. Food Chem. 54(24), 9046-9054 (2006).

    2. Nishiwaki, K., Ohigashi, K., Deguchi, T., et al. Structure-activity relationships and docking studies of hydroxychavicol and its analogs as xanthine oxidase inhibitors. Chem. Pharm. Bull. (Tokyo) 66(7), 741-747 (2018).

    3. Rajedadram, A., Pin, K.Y., Ling, S.K., et al. Hydroxychavicol, a polyphenol from Piper betle leaf extract, induces cell cycle arrest and apoptosis in TP53-resistant HT-29 colon cancer cells. J. Zhejiang Univ. Sci. B 22(2), 112-122 (2021).

    4. Pandey, A., Bani, S., Dutt, P., et al. Modulation of Th1/Th2 cytokines and inflammatory mediators by hydroxychavicol in adjuvant induced arthritic tissues. Cytokine 49(1), 114-121 (2010).

    5. Heather, M., Shimmon, R., and McDonagh, A.M. Organic impurity profiling of 3,4-methylenedioxymethamphetamine (MDMA) synthesised from catechol. Forensic Sci. Int. 248, 140-147 (2015).

    6. Yang, A.-H., Zhang, L., Zhi, D.-X., et al. Identification and analysis of the reactive metabolites related to the hepatotoxicity of safrole. Xenobiotica 48(11), 1164-1174 (2018).