A bibenzyl with diverse biological activities
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Parent Compound(s)
10004235cis-Resveratrol 70675trans-Resveratrol
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Dihydroresveratrol

Item No. 19651

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[2-(4-hydroxyphenyl)ethyl]-1,3-benzenediol
CAS Number
58436-28-5
Synonyms
  • 3,4',5-Trihydroxybibenzyl
  • α,β-Dihydro-3,4',5-trihydroxystilbene
Molecular Formula
C14H14O3
Formula Weight
230.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >50 mg/mlEthanol: >50 mg/mlPBS (pH 7.2): <100 µg/ml
λmax
226, 281 nm
SMILES
OC1=CC(CCC2=CC=C(O)C=C2)=CC(O)=C1
InChi Code
InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2
InChi Key
HITJFUSPLYBJPE-UHFFFAOYSA-N
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

    $63

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    10 mg

    $118

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    25 mg

    $213

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    50 mg

    $363

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    Cayman Chemical
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    Product Description

    Dihydroresveratrol is a polyketide synthase-derived bibenzyl that has been found in C. sativa and has diverse biological activities.1,2,3,4 It is also an active metabolite of resveratrol (Item Nos. 70675 | 10004235) that is formed by gut microbiota.5 Dihydroresveratrol inhibits DNA polymerase α but not DNA polymerase δ (Kis =29.3 and >100 µM, respectively) and the formation of thiobarbituric acid reactive substances (TBARS) in rat liver microsomes (EC50 = 1.57 µM).2 It stimulates the proliferation of hormone-sensitive MCF-7 breast cancer cells but not hormone-resistant MDA-MB-231 and BT474 breast cancer cells when used at concentrations ranging from 0.01 pM to 100 nM.3 Dihydroresveratrol decreases interalveolar septal thickness and alveolar hemorrhage in a rat model of lung injury induced by cerulein- and LPS-stimulated pancreatitis when administered at a dose of 50 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Boddington, K.F., Soubeyrand, E., Van Gelder, K., et al. Bibenzyl synthesis in Cannabis sativa L. Plant J. 109(3), 693-707 (2022).

    2. Stivala, L.A., Savio, M., Carafoli, F., et al. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. The Journal of Biological Chemisty 276(25), 22586-22594 (2001).

    3. Gakh, A.A., Anisimova, N.Y., Kiselevsky, M.V., et al. Dihydro-resveratrol—A potent dietary polyphenol. Bioorg. Med. Chem. Lett. 20(20), 6149-6151 (2010).

    4. Lin, Z.-S., Ku, C.F., Guan, Y.-F., et al. Dihydro-resveratrol ameliorates lung injury in rats with cerulein-induced acute pancreatitis. Phytother. Res. 30(4), 663-670 (2016).

    5. Bode, L.M., Bunzel, B., Huch, M., et al. In vivo and in vitro metabolism of trans-resveratrol by human gut microbiota. Am. J. Clin. Nutr. 97(2), 295-309 (2013).