A diterpenoid with diverse biological activities
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Isomer(s)
21031β-Cembrenediol
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α-Cembrenediol

Item No. 36042

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,3R,4E,8E,12S,13E)-1,5,9-trimethyl-12-(1-methylethyl)-4,8,13-cyclotetradecatriene-1,3-diol
CAS Number
57605-80-8
Synonyms
  • α-CBD
Molecular Formula
C20H34O2
Formula Weight
306.5
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble
SMILES
CC([C@H]1/C=C/[C@@](O)(C[C@H](/C=C(CC/C=C(CC1)\C)/C)O)C)C
InChi Code
InChI=1S/C20H34O2/c1-15(2)18-10-9-16(3)7-6-8-17(4)13-19(21)14-20(5,22)12-11-18/h7,11-13,15,18-19,21-22H,6,8-10,14H2,1-5H3/b12-11+,16-7+,17-13-/t18-,19+,20-/m1/s1
InChi Key
RIVKDDXPCFBMOV-WITOTENYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    25 mg

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    Product Description

    α-Cembrenediol is a diterpenoid that has been found in N. tabacum and has diverse biological activities.1,2,3,4 It inhibits induction of the early antigen of Epstein-Barr virus (EA-EBV) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells (IC50 = 25.2 μM).2 α-Cembrenediol is active against the plant pathogenic fungus V. mali (IC50 = 18 mg/L).3 Dermal application of α-cembrenediol (3.3 µmol) reduces the tumor promoting effects of TPA on 7,12-demethylbenz[a]anthracene-induced papilloma formation by 53% in mice.4 It has been found in cigarette smoke condensate.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sui, J., Wang, C., Liu, X., et al. Formation of α- and β-cembratriene-diols in tobacco (Nicotiana tabacum L.) is regulated by jasmonate-signaling components via manipulating multiple cembranoid synthetic genes. Molecules 23(10), 2511 (2018).

    2. Saito, Y., Tsujino, Y., Kaneko, H., et al. Inhibitory effects of cembratriene-4,6-diol derivatives on the induction of Epstein-Barr virus early antigen by 12-O-tetradecanoylphorbol-13-acetate. Agric. Biol. Chem. 51(3), 941-943 (1987).

    3. Yan, N., Du, Y., Liu, X., et al. Analyses of effects of α-cembratrien-diol on cell morphology and transcriptome of Valsa mali var. mali. Food Chem. 214, 110-118 (2017).

    4. Saito, Y., Takizawa, H., Konishi, S., et al. Identification of cembratriene-4,6-diol as antitumor-promoting agent from cigarette smoke condensate. Carcinogenesis 6(8), 1189-1194 (1985).