beta-eudesmol

b-selinenol

CAS: 473-15-4 C15 H26 O MW: 222.37142000 woody

Identification

Namebeta-eudesmol
IUPAC2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-ol
CAS Number473-15-4
FDA UNII6R61524P48
Molecular FormulaC15 H26 O
Molecular Weight222.37142000
MDL NumberMFCD00210502
Nikkaji NumberJ12.133I
Beilstein5735560

Regulatory

Physical Properties

Appearance pale beige powder (est)
Assay 92.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 72.00 to 74.00 °C. @ 760.00 mm Hg
Boiling Point 301.00 to 302.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.000100 mmHg @ 25.00 °C. (est)
Flash Point 227.00 °F. TCC ( 108.33 °C. )
logP (o/w) 4.568 (est)
Soluble in alcohol
Insoluble in water

Organoleptic Properties

Odor Description at 100.00 %.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-mouse LD50 > 2000 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for beta-eudesmol usage levels up tonot for fragrance use.
Recommendation for beta-eudesmol flavor usage levels up tonot for flavor use.

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Potential Uses

FR chypre FR green FR herbal FR moss FR oriental FR woody

Natural Occurrence

amyris wood oil @ 16.80% Data angelica root oil @ 0.49% Data angelica seed oil CO2 extract @ 1.50% Data basil flower oil sweet @ 0.06% Data basil leaf oil sweet (ocimum basilicum) @ 0.08% Data basil shoot oil bay laurel leaf bay laurel leaf oil burdock leaf cajuput oil vietnam @ 0.7% Data callitris columellaris wood oil australia @ 7.50% Data callitris glaucophylla wood oil australia @ 10.00% Data callitris intratropica wood oil australia @ 14.40% Data camel grass oil @ 1.10% Data cascarilla bark oil @ 3.03% Data celery seed cistus oil @ 0.4% Data citronella oil zimbabwe @ 0.49% Data clary sage oil greece @ 1.50% Data clary sage oil spain @ 0.73% Data curry fruit oil india @ <0.05% Data curry leaf oil india @ 0.20% Data dill oil eucalyptus globulus bicostata oil @ 0.26% Data eucalyptus globulus bud oil @ 0.18% Data eucalyptus globulus fruit oil @ 0.84% Data eucalyptus globulus maidenii f. muell oil @ 0.12% Data eucalyptus globulus oil @ 0.40% Data eucalyptus globulus oil burundia @ 1.30% Data eucalyptus globulus oil rwanda @ 0.11% Data eucalyptus globulus oil zambia @ 0.40% Data eucalyptus globulus pseudoglobulus oil @ 8.65% Data ferula cupularis leaf oil @ 1.66% Data geranium leaf oil india @ 0.38% Data geranium petiole oil india @ 0.23% Data geranium stem oil india @ 0.39% Data ginger rhizome ginger rhizome oil ginkgo biloba heart wood ginkgo biloba wood guaiacwood oil @ 0.18% Data guava fruit oil reunion @ 0.20% Data helichrysum italicum oil america @ 0.41% Data hinoki leaf oil @ 6.54% Data ho leaf oil @ 0.11% Data hyssop oil CO2 extract @ 0.1% Data labdanum leaf oil @ 0.50% Data laurel leaf oil turkey @ 1.10% Data manuka var. eximium oil australia @ 13.80% Data manuka var. rotundifolium oil australia @ 7.10% Data mayur pankh fruit oil himalaya @ 0.50% Data microstrobos fitzgeraldii leaf oil australia @ 0.50% Data oregano shoot oil otanthus maritimus (l.) hoffmans oil greece @ 1.10% Data pepper oil black india @ trace% Data pepper tree berry oil @ 1.01% Data phoebe oil brazil @ 6.86% Data pimenta leaf oil @ 0.82% Data piper cernum vell. var. cernum yuncker leaf oil brazil @ 1.60% Data ravintsara leaf oil @ 0.05%% Data rue oil cuba @ 0.56% Data sage oil reunion @ trace% Data salvia atropatana bunge oil iran @ 0.60% Data salvia officinalis seed oil tunisia @ 0.47% Data salvia sclarea seed oil tunisia @ 1.72% Data salvia verbenaca seed oil tunisia @ 3.76% Data tanacetum annum l. oil marocco @ 0.30% Data tansy oil marocco @ 5.10% Data valerian root oil @ 0.6-6.9% Data walnut english walnut leaf water mint shoot yuzu leaf oil @ 0.15-0.21% Data

Synonyms

(2R,4aR,8aS)- decahydro-8-methylene-a,a,4a-trimethyl-2-naphthyl methanol (2R,4aR,8aS)- decahydro-8-methylene-a,a,4a-trimethyl-2-naphthylmethanol 1,2a,3,4,4a,5,6,7,8,8aa- decahydro-a,a,4ab-trimethyl-8-methylene-2-naphthalenemethanol eudesm-4(14)-en-11-ol 4(15)- eudesmen-11-ol (+)-b- eudesmol (+)-beta- eudesmol b- eudesmol 2-((2R,4aR,8aS)-4a- methyl-8-methylene-decahydro-naphthalen-2-yl)-propan-2-ol 2-[(2R,4aR,8aS)-4a- methyl-8-methylenedecahydronaphthalen-2-yl]propan-2-ol rel-2-[(2R,4aR,8aS)-4a- methyl-8-methylenedecahydronaphthalen-2-yl]propan-2-ol 2-[(2R,4aR,8aS)-4a- methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-ol 2-[(2R,4aR,8aS)-4a- methyl-8-methylidenedecahydronaphthalen-2-yl]propan-2-ol 2- naphthalenemethanol, decahydro-a,a,4a-trimethyl-8-methylene-, (2R,4aR,8aS)- b- selinenol beta- selinenol US Patents: 4,008,184 - 6,10 Dimethyl bicyclo(4,4,0)decane or decene alcohol and ester perfume compositions PubMed: Airborne Antituberculosis Activity of Eucalyptus citriodora Essential Oil. PubMed: Essential oil characterization of two Azorean Cryptomeria japonica populations and their biological evaluations. PubMed: Volatile composition and sensory properties of Indian herbal medicine-Pavonia odorata-used in Ayurveda. PubMed: GC and GC/MS analysis of essential oil composition of the endemic Soqotraen Leucas virgata Balf.f. and its antimicrobial and antioxidant activities. PubMed: Chemical composition, cytotoxicity and in vitro antitrypanosomal and antiplasmodial activity of the essential oils of four Cymbopogon species from Benin. PubMed: Headspace solid-phase microextraction-gas chromatography-mass spectrometry characterization of propolis volatile compounds. PubMed: Eudesmol isomers induce caspase-mediated apoptosis in human hepatocellular carcinoma HepG2 cells. PubMed: Chemotaxonomic importance of the essential-oil composition in two subspecies of Teucrium stocksianum Boiss. from Iran. PubMed: Evaluation of repellency of some Chinese medicinal herbs essential oils against Liposcelis bostrychophila (Psocoptera: Liposcelidae) and Tribolium castaneum (Coleoptera: Tenebrionidae). PubMed: Suites of terpene synthases explain differential terpenoid production in ginger and turmeric tissues. PubMed: [Screening and identification of an endophytic fungus from Atractylodes lancea which utilizes volatile oil selectively]. PubMed: Chemotaxonomic and micromorphological traits of Satureja montana L. and S. subspicata Vis. (Lamiaceae). PubMed: Chemical composition, antimicrobial, antioxidant and cytotoxic activity of essential oils of Plectranthus cylindraceus and Meriandra benghalensis from Yemen. PubMed: Composition and antipathogenic activities of the twig essential oil of Chamaecyparis formosensis from Taiwan. PubMed: Comparison of the effects of fungal endophyte Gilmaniella sp. and its elicitor on Atractylodes lancea plantlets. PubMed: β-Eudesmol induces JNK-dependent apoptosis through the mitochondrial pathway in HL60 cells. PubMed: Composition, antioxidant, antimicrobial and anti-wood-decay fungal activities of the twig essential oil of Taiwania cryptomerioides from Taiwan. PubMed: Antifungal Activity of the Essential Oils of Callitris neocaledonica and C. sulcata Heartwood (Cupressaceae). PubMed: Antifungal properties of Japanese cedar essential oil from waste wood chips made from used sake barrels. PubMed: Effects of an Atractylodes lancea rhizome extract and a volatile component β-eudesmol on gastrointestinal motility in mice. PubMed: A hexane fraction of guava Leaves (Psidium guajava L.) induces anticancer activity by suppressing AKT/mammalian target of rapamycin/ribosomal p70 S6 kinase in human prostate cancer cells. PubMed: In vitro and in vivo antitumor effects of the essential oil from the leaves of Guatteria friesiana. PubMed: Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. leaves. PubMed: Essential oil of Myrica esculenta Buch. Ham.: composition, antimicrobial and topical anti-inflammatory activities. PubMed: Flavonoids and sesquiterpenes from Tecurium ramosissimum promote antiproliferation of human cancer cells and enhance antioxidant activity: a structure-activity relationship study. PubMed: Composition and antifungal activities of the leaf essential oil of Neolitsea parvigemma from Taiwan. PubMed: Volatile components from aerial parts of Centaurea gracilenta and C. ovina ssp. besserana growing wild in Bulgaria. PubMed: Aroma evaluation of gamazumi (Viburnum dilatatum) by aroma extract dilution analysis and odour activity value. PubMed: Repellent constituents of essential oil of Cymbopogon distans aerial parts against two stored-product insects. PubMed: Chemical composition, antibacterial activity and cytotoxicity of essential oils of Tanacetum parthenium in different developmental stages. PubMed: Insecticidal compounds from the essential oil of Chinese medicinal herb Atractylodes chinensis. PubMed: Anti-inflammatory and antiulcerogenic activities of leaf extracts and sesquiterpene from Teucrium ramosissimum (Lamiaceae). PubMed: Composition and antimicrobial activities of the leaf essential oil of Machilus kusanoi from Taiwan. PubMed: Eucalyptus oleosa essential oils: chemical composition and antimicrobial and antioxidant activities of the oils from different plant parts (stems, leaves, flowers and fruits). PubMed: Composition and antimicrobial activity of the leaf and twig oils of Litsea mushaensis and L. linii from Taiwan. PubMed: Bioconversion of substituted naphthalenes and β-eudesmol with the cytochrome P450 BM3 variant F87V. PubMed: Composition and antifungal activities of the leaf essential oil of Litsea coreana from Taiwan. PubMed: Essential oil composition of leaves of Stachys yemenensis obtained by supercritical CO₂. PubMed: Evaluation of Moon-tang on allergic reactions. PubMed: [Effects of primary processing on quality of cortex Magnolia officinalis]. PubMed: Composition and antimicrobial and anti-wood-decay fungal activities of the leaf essential oils of Machilus pseudolongifolia from Taiwan. PubMed: New sesquiterpene coumarins from the roots of Ferula flabelliloba. PubMed: The regulatory mechanism of β-eudesmol is through the suppression of caspase-1 activation in mast cell-mediated inflammatory response. PubMed: [Simultaneous determination of atractylone, hinesol, beta-eudesmol, atrctylodin in Atractylodes lancea and hierarchical cluster analysis]. PubMed: Antimicrobial activity and chemical composition of endemic Centaurea cariensis subsp. niveo-tomentosa. PubMed: Variation in volatile leaf oils of 13 Eucalyptus species harvested from Souinet arboreta (Tunisia). PubMed: Chemical analysis and biological activity of the essential oils of two endemic Soqotri Commiphora species. PubMed: Volatile components of aerial parts of Centaurea nigrescens and C. stenolepis growing wild in the Balkans. PubMed: Variation in volatile leaf oils of twelve eucalyptus species harvested from Hajeb Layoun arboreta (Tunisia). PubMed: A new butanolide and a new secobutanolide from Litsea lii var. nunkao-tahangensis. PubMed: [Advances in chemistry, molecular biology and pharmacological of Cangzhu]. PubMed: Screening for antiviral activities of isolated compounds from essential oils. PubMed: Active compounds against tinea pedis dermatophytes from Ageratina pichinchensis var. bustamenta. PubMed: Composition and antimicrobial activity of the leaf essential oil of Litsea kostermansii from Taiwan. PubMed: Essential oil composition of two new species of Phebalium (Rutaceae) from north-eastern NSW, Australia. PubMed: Identification of volatile compounds of Atractylode lancea rhizoma using supercritical fluid extraction and GC-MS. PubMed: [Studies on chemical constituents from rhizomes of Hedychium chrysoleucum]. PubMed: Montanoa tomentosa glandular trichomes containing kaurenoic acids chemical profile and distribution. PubMed: A new cytotoxic prenylated dihydrobenzofuran derivative and other chemical constituents from the rhizomes of Atractylodes lancea DC. PubMed: Chemical composition and antimicrobial activity of the essential oils of the Amazon Guatteriopsis species. PubMed: Interference of beta-eudesmol in nestmate recognition in Atta sexdens rubropilosa (Hymenoptera: Formicidae). PubMed: [Determination of beta-eudesmol in rhizome of Atractylodes lancea by RP-HPLC]. PubMed: Terpenoid compositions, and antioxidant and antimicrobial properties of the rhizome essential oils of different Hedychium species. PubMed: Beta-eudesmol suppresses tumour growth through inhibition of tumour neovascularisation and tumour cell proliferation. PubMed: Isolation and functional characterization of a beta-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith. PubMed: Reversal of cocaine-induced planarian behavior by parthenolide and related sesquiterpene lactones. PubMed: Essential oil composition of Teucrium scordium L. PubMed: [Fingerprint of volatile oil of Atractylodes lancea by GC-MS]. PubMed: Essential oil composition of the different parts of Eryngium corniculatum Lam. (Apiaceae) from Spain. PubMed: Chemical composition and antimicrobial activity of the essential oil of Teucrium ramosissimum (Lamiaceae). PubMed: Volatile organic compounds of Angelica gigas Nakai, Korean medicinal herb. PubMed: Antimicrobial activity of the essential oil and extracts of Cordia curassavica (Boraginaceae). PubMed: Chemical composition and in vitro antifungal and antioxidant activity of the essential oil and methanolic extract of Teucrium sauvagei Le Houerou. PubMed: [Development of anti-dementia drugs related to neurotrophic factors]. PubMed: Qualitative and quantitative analysis of the active components of the essential oil from Brickellia veronicaefolia by nuclear magnetic resonance spectroscopy. PubMed: Constituents of Salvia microphylla. PubMed: Medical benefits of using natural compounds and their derivatives having multiple pharmacological actions. PubMed: Analysis of the essential oil composition of eight Anthemis species from Greece. PubMed: Composition and antimicrobial activity of essential oils from Centaurea sessilis and Centaurea armena. PubMed: Analysis of hop-derived terpenoids in beer and evaluation of their behavior using the stir bar-sorptive extraction method with GC-MS. PubMed: Antiangiogenic activity of beta-eudesmol in vitro and in vivo. PubMed: Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species. PubMed: Eudesmane sesquiterpenes from the aquatic fungus Beltrania rhombica. PubMed: [Studies on chemical constituents in essential oil from wild Atractylodes lancea in dabie mountains]. PubMed: Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures. PubMed: Behavioral changes in workers of the leaf-cutting ant Atta sexdens rubropilosa induced by chemical components of Eucalyptus maculata leaves. PubMed: Beta-eudesmol, a new sesquiterpene component in intact and organized root of chamomile (Chamomilla recutita). PubMed: Effect of storage on the essential oil composition of Piper nigrum L. fruits of different ripening states. PubMed: Ovicidal and adulticidal activity of Eucalyptus globulus leaf oil terpenoids against Pediculus humanus capitis (Anoplura: Pediculidae). PubMed: New terpenoids in cultivated and wild chamomile (in vivo and in vitro). PubMed: Correlations between pulp properties of eucalyptus clones and leaf volatiles using automated solid-phase microextraction. PubMed: [The naphtha composing characteristics of geoherbs of Atractylodes lancea]. PubMed: Volatile compounds from leaf-buds of Populus nigra L (Salicaceae). PubMed: [Methodological studies on quantitative determination of beta-eudesmol in Atractylodes lancea (thunb.) DC]. PubMed: [GC-MS analysis of essential oils from rhizomes of Atractylodes lancea (Thunb.) DC. and A. chinensis (DC.) Koidz]. PubMed: Effect of the rhizomes of Atractylodes lancea and its constituents on the delay of gastric emptying. PubMed: [Analysis of constituents of essential oil from Anemone altaica Fisch. ex C. A. Mey]. PubMed: Effect of drying method on the volatiles in bay leaf (Laurus nobilis L.). PubMed: Beta-eudesmol induces neurite outgrowth in rat pheochromocytoma cells accompanied by an activation of mitogen-activated protein kinase. PubMed: Chemical analysis and antimicrobial activity of Halimium voldii. PubMed: Microbiological conversion of a beta- and gamma-eudesmol mixture by Rhizopus. PubMed: Effects of constituents from the bark of Magnolia obovata on nitric oxide production in lipopolysaccharide-activated macrophages. PubMed: Seasonal variation in chemical constituents of Santolina rosmarinifolia L. ssp. rosmarinifolia. PubMed: [Phytochemical study of liverworts Conocephalum conicum and Chiloscyphus polyanthos]. PubMed: Chemical constituents of two Chinese Magnoliaceae plants, Tsoongiodendron odorum and Manglietiastrum sinicum, and their inhibition of platelet aggregation. PubMed: Effects of extract and ingredients isolated from Magnolia obovata thunberg on catecholamine secretion from bovine adrenal chromaffin cells. PubMed: Eudesmanoids from Sphaeranthus indicus. PubMed: [Studies on the essential oil constituents of the stem bark of Magnolia obovata]. PubMed: The essential oil of Senecio graveolens (Compositae): chemical composition and antimicrobial activity tests. PubMed: Atractylodes lancea autotetraploids induced by colchicine treatment of shoot cultures. PubMed: Chinese herb constituent beta-eudesmol alleviated the electroshock seizures in mice and electrographic seizures in rat hippocampal slices. PubMed: Random amplified polymorphic DNA analysis and variation of essential oil components of Atractylodes plants. PubMed: A comparative study on essential oil components of wild and cultivated Atractylodes lancea and A. chinensis. PubMed: [Study of components in crude drugs by headspace gas chromatography. II. Components of atractylodes]. PubMed: Potentiating effects of beta-eudesmol-related cyclohexylidene derivatives on succinylcholine-induced neuromuscular block in isolated phrenic nerve-diaphragm muscles of normal and alloxan-diabetic mice. PubMed: beta-Eudesmol as an antidote for intoxication from organophosphorus anticholinesterase agents. PubMed: Structural components of beta-eudesmol essential for its potentiating effect on succinylcholine-induced neuromuscular blockade in mice. PubMed: [Analysis of chemical constituents of essential oil from dechengqi decoction]. PubMed: Different modes of potentiation by beta-eudesmol, a main compound from Atractylodes lancea, depending on neuromuscular blocking actions of p-phenylene-polymethylene bis-ammonium derivatives in isolated phrenic nerve-diaphragm muscles of normal and alloxan-diabetic mice. PubMed: Interaction of beta-eudesmol with Na+,K(+)-ATPase: inhibition of K(+)-pNPPase activity. PubMed: Inhibition of Na+,K(+)-ATPase activity by beta-eudesmol, a major component of atractylodis lanceae rhizoma, due to the interaction with enzyme in the Na.E1 state. PubMed: Antagonism by beta-eudesmol of neostigmine-induced neuromuscular failure in mouse diaphragms. PubMed: Blocking action of succinylcholine with beta-eudesmol on acetylcholine-activated channel activity at endplates of single muscle cells of adult mice. PubMed: Mechanism of the blocking action of beta-eudesmol on the nicotinic acetylcholine receptor channel in mouse skeletal muscles. PubMed: Medicinal Plants from Papua New Guinea: Graniline-Esters and Germacranolides from Blumea arfakiana. PubMed: Enhancing effect by nicotinic acetylcholine receptor channel blockers, including beta-eudesmol, on succinylcholine-induced inhibition of twitch tension and intracellular Ca++ in mouse diaphragm muscle. PubMed: Noncontractile acetylcholine receptor-operated Ca++ mobilization: suppression of activation by open channel blockers and acceleration of desensitization by closed channel blockers in mouse diaphragm muscle. PubMed: Botanical and chemical evaluation of Atractylodes lancea plants propagated in vitro and by division of the rhizome. PubMed: Antianoxic action and active constituents of atractylodis lanceae rhizoma. PubMed: Intestinal motility enhancing effect of Atractylodes lancea rhizome. PubMed: beta-eudesmol (a main component of Atractylodes lancea)-induced potentiation of depolarizing neuromuscular blockade in diaphragm muscles of normal and diabetic mice. PubMed: Sesquiterpene Glycosides from Calendula persica. PubMed: A Further Contribution to the Sesquiterpenoid Constituents of Cymbopogon proximus. PubMed: Studies on the origin, processing and quality of crude drugs. II. Pharmacological evaluation of the Chinese crude drug "zhu" in experimental stomach ulcer. (2). Inhibitory effect of extract of Atractylodes lancea on gastric secretion. PubMed: Volatile Constituents of Artemisia nilagirica. PubMed: Antihepatotoxic principles of Atractylodes rhizomes. PubMed: Composition of essential oils of Laurus nobilis, L. nobilis var. angustifolia and Laurus azorica. PubMed: Hypotensive activity of beta-eudesmol and some related sesquiterpenes. PubMed: Studies leading to the stereoselective total synthesis of dl-beta-eudesmol, dl-beta-selinene, dl-costol, and related naturally occurring sesquiterpenes.