A sesquiterpene with diverse biological activities
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β-Eudesmol

Item No. 25771

Technical Information
Formal Name
(2R,4aR,8aS)-decahydro-α,α,4a-trimethyl-8-methylene-2-naphthalenemethanol
CAS Number
473-15-4
Synonyms
  • (+)-β-Eudesmol
Molecular Formula
C15H26O
Formula Weight
Purity
≥95%
Formulation
A solid
Chloroform: Slightly SolubleChloroform: Slightly SolubleMethanol: Slightly SolubleMethanol: Slightly Soluble
SMILES
C=C1[C@@]2([H])[C@](CC[C@@H](C(O)(C)C)C2)(C)CCC1
InChi Code
InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h12-13,16H,1,5-10H2,2-4H3/t12-,13+,15-/m1/s1
InChi Key
BOPIMTNSYWYZOC-VNHYZAJKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    β-Eudesmol is a sesquiterpene that has been found in a variety of plants, including Cannabis, and has diverse biological activities.1,2 It is a noncompetitive antagonist of nicotinic acetylcholine receptors (nAChRs) that decreases the open time and opening frequency of nAChR channels when used at concentrations of 40 and 80 µM and increases the decay phase of depolarization when used at a concentration of 100 µM in isolated mouse diaphragm muscle.3 β-Eudesmol (50-100 µM) inhibits VEGF- and bFGF-induced proliferation in human umbilical vein endothelial cells (HUVECs).4 It also inhibits proliferation of HeLa, SGC-7901, and BEL-7402 cells when used at concentrations ranging from 10 to 100 µM and reduces tumor growth in H22 and S-180 mouse tumor models when administered at doses ranging from 2.5 to 5 mg/kg. β-Eudesmol is an agonist of the transient receptor potential (TRP) receptor subtypes TRPA1, TRPV3, and TRPM8 and increases food intake and plasma levels of ghrelin in rats.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Elzinga, S., Fischedick, J., Podkolinski, R., et alCannabinoids and terpenes as chemotaxonomic markers in Cannabis. Nat. Prod. Chem. Res. 3(4), 181 (2015).

    2. Kimura, I. Medical benefits of using natural compounds and their derivatives having multiple pharmacological actions. Yakugaku Zasshi 126(3), 133-143 (2006).

    3. Kimura, M., Nojima, H., Muroi, M., et alMechanism of the blocking action of β-eudesmol on the nicotinic acetylcholine receptor channel in mouse skeletal muscles. Neuropharmacology 30(8), 835-841 (1991).

    4. Ma, E.L., Li, Y.C., Tsuneki, H., et alβ-Eudesmol suppresses tumour growth through inhibition of tumour neovascularisation and tumour cell proliferation. J. Asian Nat. Prod. Res. 10(1-2), 159-167 (2008).

    5. Ohara, K., Fukada, T., Okada, H., et alIdentification of significant amino acids in multiple transmembrane domains of human transient receptor potential ankyrin 1 (TRPA1) for activation by eudesmol, an oxygenized sesquiterpene in hop essential oil. The Journal of Biological Chemisty 290(5), 3161-3171 (2015).

    6. Ohara, K., Fukuda, T., Ishida, Y., et alβ-Eudesmol, an oxygenized sesquiterpene, stimulates appetite via TRPA1 and the autonomic nervous system. Sci. Rep. 7(1), 15785 (2017).