A methylcatechol with diverse biological activities
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4-Methylcatechol

Item No. 36429

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-methyl-1,2-benzenediol
CAS Number
452-86-8
Synonyms
  • 1,2-Dihydroxy-4-methylbenzene
  • 3,4-Dihydroxytoluene
  • Homocatechol
  • 2-Hydroxy-4-methylphenol
  • 4-Methylpyrocatechol
  • NSC 17489
  • p-Methylcatechol
Molecular Formula
C7H8O2
Formula Weight
124.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 20 mg/mlEthanol: 3 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
OC1=CC=C(C)C=C1O
InChi Code
InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
InChi Key
ZBCATMYQYDCTIZ-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $31

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    50 g

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    Product Description

    4-Methylcatechol is a methylcatechol with diverse biological activities and an active metabolite of the flavonoid quercetin (Item No. 10005169).1,2,3 It is formed from quercetin by gut microbiota.1 4-Methylcatechol inhibits migration of, and induces cell cycle arrest in the G2/M phase, production of reactive oxygen species (ROS), and apoptosis in, 1205Lu melanoma cells when used at concentrations of 10 and 25 µg/ml.2 It induces relaxation of isolated rat aortic rings and mesenteric arteries (EC50s = 49.1 and 21.2 µM, respectively) and reduces blood pressure in spontaneously hypertensive stroke-prone (SHRSP) rats.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhao, L., Qi, Z., Yi, L., et al. The interaction between gut microbiota and flavonoid extract from Smilax glabra Roxb. and its potent alleviation of fatty liver. Food Funct. 12(17), 7836-7850 (2021).

    2. Payton, F., Bose, R., Alworth, W.L., et al. 4-methylcatechol-induced oxidative stress induces intrinsic apoptotic pathway in metastatic melanoma cells. Biochem. Pharmacol. 81(10), 1211-1218 (2011).

    3. Pourová, J., Najmanová, I., Vopršalová, M., et al. Two flavonoid metabolites, 3,4-dihydroxyphenylacetic acid and 4-methylcatechol, relax arteries ex vivo and decrease blood pressure in vivo. Vascul. Pharmacol. 111, 36-43 (2018).