A phenol and microbial metabolite with diverse biological activities
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3-Chlorogentisyl Alcohol

Item No. 40663

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-chloro-6-(hydroxymethyl)-1,4-benzenediol
CAS Number
32744-80-2
Molecular Formula
C7H7ClO3
Formula Weight
174.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly Soluble: 1-10 mg/mlEthanol: Sparingly Soluble: 1-10 mg/mlPBS (pH 7.2): Sparingly Soluble: 1-10 mg/ml
SMILES
OC1=CC(CO)=C(O)C(Cl)=C1
InChi Code
InChI=1S/C7H7ClO3/c8-6-2-5(10)1-4(3-9)7(6)11/h1-2,9-11H,3H2
InChi Key
GUIGFYWMQAYTBT-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $32

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    5 mg

    $88

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    10 mg

    $145

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    Product Description

    3-Chlorogentisyl alcohol is a phenol and microbial metabolite that has been found in Ampelomyces and has diverse biological activities.1,2,3 It scavenges DPPH (Item No. 14805) radicals in a cell-free assay (IC50 = 1 µM).2 3-Chlorogentisyl alcohol is active against methicillin-resistant S. aureus (MRSA; MIC = 50 µg/ml), as well as 13 Gram-positive and Gram-negative bacteria when used at a concentration of 50 µg/disc.2,1 3-Chlorogentisyl alcohol has concentration-dependent antifouling activity against barnacle (B. amphitrite) cyprids in the conventional submerged assay using polystyrene plates. It induces apoptosis and cell cycle arrest at the S phase in HeLa cervical cancer cells when used at a concentration of 50 µM.3 3-Chlorogentisyl alcohol (35 µM) induces ssDNA breaks in a comet assay using HeLa cells.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kwong, T.F.N., Miao, L., Li, X., et al. Novel antifouling and antimicrobial compound from a marine-derived fungus Ampelomyces sp. Mar. Biotechnol. (NY) 8(6), 634-640 (2006).

    2. Li, Y., Li, X., and Son, B.W. Antibacterial and radical scavenging epoxycyclohexenones and aromatic polyols from a marine isolate of the fungus Aspergillus. Nat. Prod. Sci. 11(3), 136-138 (2005).

    3. Zhang, Y., Ahn, E.-Y., Jiang, Y., et al. 3-Chloro-2,5-dihydroxybenzyl alcohol activates human cervical carcinoma HeLa cell apoptosis by inducing DNA damage. Int. J. Oncol. 31, 1317-1323 (2007).