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17790

Sigma-Aldrich

β-Eudesmol

≥90% (GC)

Synonym(s):

(2R,4aR,8aS)-Decahydro-8-methylene-α,α,4a-trimethyl-2-naphthylmethanol

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About This Item

Empirical Formula (Hill Notation):
C15H26O
CAS Number:
Molecular Weight:
222.37
Beilstein:
5735560
MDL number:
UNSPSC Code:
12352212
PubChem Substance ID:
NACRES:
NA.25

Quality Level

Assay

≥90% (GC)

form

powder

mp

72-74 °C (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

[H][C@@]12C[C@@H](CC[C@@]1(C)CCCC2=C)C(C)(C)O

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

General description

β-Eudesmol is an aromatic, oxygenated sesquiterpene compound. It is primarily observed in the bark of mangolia trees and can also be extracted from other medical herbs such as Cryptomeria japonica, Atractylodes lancea, Pterocarpus santalinus, Ginkgo biloba, and Nardostachys jatamansi.

Application

β-Eudesmol has been used:
  • as a treatment to test its antioxidant, anti-inflammatory, cell preservation effects on human dermal fibroblasts (HDFs)
  • as a reference standard to investigate if metabolically engineered E. coli extracted terpene synthase (Tps) genes encode for β-eudesmol synthase by using gas chromatography-mass spectrometry (GC/MS) analysis
  • to test its antiviral effects against herpes simplex virus type 1 (HSV-1)
  • to test its reversal effects of cocaine-induced planarian behavior

Biochem/physiol Actions

β-Eudesmol has many pharmacological benefits. It is an active ingredient present in many essential oils, showing antioxidant and antimicrobial activities. β-Eudesmol elicits its antifungal and anti-wood-decay fungal activities in leaf essential oil of Litsea coreana tree, and the twigs of Taiwania cryptomerioides trees respectively. It suppresses tumor cell proliferation, growth, and migration of human tumor cells. β-Eudesmol is known to have various protective effects on the nervous system.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bioconversion of various substituted naphthalenes that contain 1-methoxy- and 1-ethoxy-naphthalenes, methylnaphthalenes, dimethylnaphthalenes, and naphthalenecarboxylic acid methyl esters were performed using recombinant Escherichia coli cells, which expressed the gene coding for a cytochrome P450 BM3 variant F87V (P450 BM3 (F87V)) that
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Journal of oleo science, 67(10), 1235-1246 (2018-10-12)
Terpene synthase (TPS) genes were isolated and functionally characterized from three traditional edible plants, Acanthopanax sciadophylloides ("Koshiabura") and Acanthopanax sieboldianus ("Himeukogi"), belonging to the family Araliaceae, and Curcuma zedoaria (zedoary, "Gajutsu"), belonging to the family Zingiberaceae. These plants emit characteristic
C G S Marinho et al.
Bulletin of entomological research, 98(5), 467-473 (2008-04-29)
Leaf-cutter ant species (Atta spp.) are key pests of cultivated crops in the Neotropics, and recent studies have demonstrated that workers of Atta spp., particularly of Atta sexdens rubropilosa, exhibit aggressive behavior among nestmates when in contact with the sesquiterpene
Chen-Lung Ho et al.
Natural product communications, 7(2), 261-264 (2012-04-06)
This study investigated the chemical composition, antioxidant, antimicrobial and anti-wood-decay fungal activities of the essential oil isolated from the twigs of Taiwania cryptomerioides from Taiwan. The essential oil was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID
Antimicrobial and antioxidant activities and gas chromatography mass spectrometry (GC/MS) analysis of the essential oils of Ajuga bracteosa Wall. ex Benth. and Lavandula dentata L. growing wild in Yemen
Mothana RA, et al.,
Journal of Medicinal Plants Research, 6(15), 3066-3071 (2012)

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