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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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Chen-Lung Ho et al.
Natural product communications, 5(7), 1143-1146 (2010-08-26)
The hydrodistillated leaf essential oil of Machilus pseudolongifolia was analyzed to determine its composition and yield. Seventy compounds were identified, the main components being beta-eudesmol (26.8%), alpha-cadinol (20.8%), viridiflorene (8.9%), alpha-caryophyllene (5.3%), globulol (4.6%) and beta-caryophyllene (4.2%). Oxygenated sesquiterpenes (60.1%)
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)
Jean Waikedre et al.
Chemistry & biodiversity, 9(3), 644-653 (2012-03-17)
Mortality due to fungal infections has increased substantially, becoming a worldwide problem in public health. As a contribution to the discovery of new antifungal agents, the properties of the heartwood essential oils of two trees growing in New Caledonia, Callitris
Chen-Lung Ho et al.
Natural product communications, 5(10), 1677-1680 (2010-12-03)
The hydrodistilled leaf essential oil of Litsea coreana was analyzed by GC/FID and GC/MS. Fifty-two compounds were identified, the main components being n-decanal (27.5%), 2E,6E-farnesol (25.8%), beta-eudesmol (10.3%), ethyl n-dodecanoate (8.0%) and tau-cadinol (6.6%). Oxygenated sesquiterpenes (56.8%) and non-terpenoids (37.0%)
Min-Jun Seo et al.
Immunopharmacology and immunotoxicology, 33(1), 178-185 (2010-07-08)
β-Eudesmol is sesquiterpenoid alcohol which contains the rhizome of Atractylodes lancea. Although it has multiple pharmacological effects, the anti-inflammatory effect of β-eudesmol and its molecular mechanisms are poorly elucidated. In this study, we investigated the regulatory mechanism of β-eudesmol on

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