beta-cadinene

(1S,4aR,8aS)-1-isopropyl-4,7-dimethyl-1,2,4a,5,8,8a-hexahydronaphthalene

CAS: 523-47-7 C15 H24 MW: 204.35628000 woody

Identification

Namebeta-cadinene
IUPAC(1S,4aR,8aS)-4,7-dimethyl-1-propan-2-yl-1,2,4a,5,8,8a-hexahydronaphthalene
CAS Number523-47-7
FDA UNIIZ07LA0GY4J
Molecular FormulaC15 H24
Molecular Weight204.35628000
Nikkaji NumberJ6.632J

Regulatory

Physical Properties

Appearance colorless clear viscous liquid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 273.00 to 276.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.011000 mmHg @ 25.00 °C. (est)
Flash Point 224.00 °F. TCC ( 106.67 °C. )
logP (o/w) 6.434 (est)
Soluble in alcohol
Insoluble in water

Organoleptic Properties

Odor Description at 100.00 %.

Safety Information

Oral/Parenteral ToxicityNot determined
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-cadinene usage levels up tonot for fragrance use.
Recommendation for beta-cadinene flavor usage levels up tonot for flavor use.

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Potential Uses

FR amyris

Natural Occurrence

basil plant bay leaf oil @ 0.00-<0.01% Data calamus root oil @ 1.57% Data cananga oil china @ 0.16% Data dacrydium colensol ginger lavender oil spike spain @ 0.01% Data oregano plant thyme oil wormwood flower oil annus america @ 0.37% Data wormwood leaf oil annus america @ 0.18-0.50% Data zingiber officinale root oil china @ 8.72% Data

Synonyms

cadine-3,9-diene (-)-beta- cadinene b- cadinene (1S,4aR,8aS)-4,7- dimethyl-1-(1-methylethyl)-1,2,4a,5,8,8a-hexahydronaphthalene (1S,4aR,8aS)-4,7- dimethyl-1-(propan-2-yl)-1,2,4a,5,8,8a-hexahydronaphthalene (1S,4aR,8aS)-4,7- dimethyl-1-propan-2-yl-1,2,4a,5,8,8a-hexahydronaphthalene (1S- (1alpha,4abeta, 8aalpha))- 1,2,4a,5,8,8a- hexahydro-4,7-dimethyl-1-(1-methyl ethyl) naphthalene (1S,4aR,8aS)-1,2,4a,5,8,8a- hexahydro-4,7-dimethyl-1-(1-methylethyl)naphthalene [1S-(1a,4ab,8aa)]-1,2,4a,5,8,8a- hexahydro-4,7-dimethyl-1-(1-methylethyl)naphthalene naphthalene, 1,2,4a,5,8,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S,4aR,8aS)- (1S,4aR,8aS)-1-iso propyl-4,7-dimethyl-1,2,4a,5,8,8a-hexahydronaphthalene PubMed: Lavender (Lavandula stoechas L.) essential oils attenuate hyperglycemia and protect against oxidative stress in alloxan-induced diabetic rats. PubMed: Screening of natural compounds as activators of the keap1-nrf2 pathway. PubMed: Mechanism of ion transfer in supported liquid membrane systems: electrochemical control over membrane distribution. PubMed: Analysis of essential oil constituents of three Dasymaschalon species (Annonaceae) from Vietnam. PubMed: Absolute configuration of falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol) from Pastinaca sativa. PubMed: Study on Gas Chromatography-Mass Spectrometry Fingerprint of Acanthopanax brachypus. PubMed: Enhancement of 4-acetylantroquinonol B production by supplementation of its precursor during submerged fermentation of Antrodia cinnamomea. PubMed: Mitigation of radiation-induced damage by targeting EGFR in noncancerous human epithelial cells. PubMed: Characterization of posticlure and the structure-related sex pheromone candidates prepared by epoxidation of (6Z,9Z,11E)-6,9,11-trienes and (3Z,6Z,9Z,11E)-3,6,9,11-tetraenes. PubMed: Photoinduced reactions of para-quinones with bicyclopropylidene leading to diverse polycyclic compounds with spirocyclopropanes. PubMed: Chemical composition and anti-Trypanosoma cruzi activity of essential oils obtained from leaves of Xylopia frutescens and X. laevigata (Annonaceae). PubMed: Cadinene sesquiterpenes from Eupatorium adenophorum and their antifungal activity. PubMed: Chemical constituents and anticancer effects of the essential oil from leaves of Xylopia laevigata. PubMed: A new eudesmane sesquiterpenoid lactone from Chloranthus japonicus. PubMed: Analysis of chemical constituents and antinociceptive potential of essential oil of Teucrium Stocksianum bioss collected from the North West of Pakistan. PubMed: Distillation time alters essential oil yield, composition, and antioxidant activity of male Juniperus scopulorum trees. PubMed: Investigation of the volatile constituents of different Gynura species from two Chinese origins by SPME/GC-MS. PubMed: Penta-cyclo-[9.3.1.1(2,6).1(4,8).1(9,13)]octa-deca-1(2),8(9)-diene. PubMed: Validation of the multiple sensor mechanism of the Keap1-Nrf2 system. PubMed: Methyl 2,2-dimeth-oxy-8-oxo-1-oxaspiro-[4.5]deca-6,9-diene-3-carboxyl-ate. PubMed: Chemical composition, antimicrobial and antitumor activities of the essential oils and crude extracts of Euphorbia macrorrhiza. PubMed: Influence of various growth parameters on fungal growth and volatile metabolite production by indoor molds. PubMed: The use of in vitro technologies and high-resolution/accurate-mass LC-MS to screen for metabolites of 'designer' steroids in the equine. PubMed: The use of in vitro technologiesand high-resolution/accurate-mass LC-MSto screen for metabolites of 'designer' steroids in the equine. PubMed: Antiplasmodial volatile extracts from Cleistopholis patens Engler & Diels and Uvariastrum pierreanum Engl. (Engl. & Diels) (Annonaceae) growing in Cameroon. PubMed: Immunotoxicity activity of sesquiterpenoids from black galingale (Kaempferia parviflora Wall. Ex. Baker) against Aedes aegypti L. PubMed: Essential oil composition and insecticidal activity of Blumea perrottetiana growing in southwestern Nigeria. PubMed: Biological activity of the essential oil of Kadsura longipedunculata (Schisandraceae) and its major components. PubMed: Comparative in vitro metabolism of the 'designer' steroid estra-4,9-diene-3,17-dione between the equine, canine and human: identification of target metabolites for use in sports doping control. PubMed: [Research on liposoluble ingredients of Quchiling]. PubMed: 5-Methyl-2,4-bis-(methyl-sulfan-yl)tricyclo-[6.2.1.0]undeca-4,9-diene-3,6-dione. PubMed: Determination of cobalt ions at nano-level based on newly synthesized pendant armed macrocycle by polymeric membrane and coated graphite electrode. PubMed: Fingerprint of selected Salvia species by HS-GC-MS analysis of their volatile fraction. PubMed: Chemical composition and antimicrobial activity of the essential oil of Anaphalis nubigena var. monocephala. PubMed: Crystal structure of (+)-delta-cadinene synthase from Gossypium arboreum and evolutionary divergence of metal binding motifs for catalysis. PubMed: Sesquiterpenes from Laurencia similis. PubMed: Instrumental analysis of terminal-conjugated dienes for reexamination of the sex pheromone secreted by a nettle moth, Parasa lepida lepida. PubMed: (8S,9R,10S,11S,13S,14S,16S,17R)-4,4-Dichloro-16β-methyl-3,20-dioxo-17,21-bis-(propano-yloxy)-5β,8β-epoxy-pregna-1,9-diene. PubMed: Cuticular hydrocarbons and soldier defense secretions of Reticulitermes in southern California: a critical analysis of the taxonomy of the genus in North America. PubMed: Inhibition of mitochondrial metabolism by methyl-2-cyano-3,12-dioxooleana-1,9-diene-28-oate induces apoptotic or autophagic cell death in chronic myeloid leukemia cells. PubMed: Tricyclo-[6.2.1.0]undeca-4,9-diene-3,6-dione. PubMed: Suppressing the thermal metacyclophanediene to dihydropyrene isomerization: synthesis and rearrangement of 8,16-dicyano[2.2]metacyclophane-1,9-diene and evidence supporting the proposed biradicaloid mechanism. PubMed: Two new xeniolides from a Taiwanese Xenia soft coral. PubMed: A one-pot, microwave-influenced synthesis of diverse small molecules by multicomponent reaction cascades. PubMed: Glucocorticoid receptor activation is involved in producing abnormal phenotypes of single-prolonged stress rats: a putative post-traumatic stress disorder model. PubMed: Involvement of glucocorticoid receptor and pregnane X receptor in the regulation of mouse CYP3A44 female-predominant expression by glucocorticoid hormone. PubMed: Synthesis and identification of novel oxa-steroids as progesterone receptor antagonists. PubMed: Ab initio and DFT investigation of electrophilic addition reaction of bromine to endo,endo-tetracyclo[4.2.1.1(3,6).0 (2,7)]dodeca-4,9-diene. PubMed: An evaluation of the allelopathic potential of selected perennial groundcovers: foliar volatiles of catmint (Nepeta x faassenii) inhibit seedling growth. PubMed: Transport of a hydrophobic biosynthetic precursor by lipophorin in the hemolymph of a geometrid female moth which secretes an epoxyalkenyl sex pheromone. PubMed: Xenicane-type diterpenes with cytotoxicity from Xenia florida. PubMed: Analysis of atmospheric sesquiterpenes: sampling losses and mitigation of ozone interferences. PubMed: Intramolecular hydrogen bonding in depsipeptides containing endo-3,6-tricyclo[6.2.1.0(2,7)]undeca-4,9-diene-3,6-endo-diol. PubMed: A novel mechanism of action of methyl-2-cyano-3,12 dioxoolean-1,9 diene-28-oate: direct permeabilization of the inner mitochondrial membrane to inhibit electron transport and induce apoptosis. PubMed: Panaxynol induces neurite outgrowth in PC12D cells via cAMP- and MAP kinase-dependent mechanisms. PubMed: Sex pheromone and related compounds in the Ishigaki and Okinawa strains of the tussock moth Orgyia postica (Walker) (Lepidoptera: Lymantriidae). PubMed: Identification of a sex pheromone component of the geometrid moth Milionia basalis pryeri. PubMed: Identification of sex pheromone components of the painted apple moth: a tussock moth with a thermally labile pheromone component. PubMed: Sesquiterpene constituents from the essential oils of the liverworts Mylia taylorii and Mylia nuda. PubMed: Photochemical study of [3(3)](1,3,5)cyclophane and emission spectral properties of [3n]cyclophanes (n = 2-6). PubMed: The sesquiterpene hydrocarbons of maize (Zea mays) form five groups with distinct developmental and organ-specific distributions. PubMed: Oxygenated bisabolane fucosides from Carthamus lanatus L. PubMed: Novel diterpenes from the heartwood of Chamaecyparis obtusa var. formosana. PubMed: Three new sesquiterpenes from the black heartwood of Cryptomeria japonica. PubMed: Development of the selective progesterone receptor modulator CDB-2914 for clinical indications. PubMed: Pharmacologic properties of CDB(VA)-2914. PubMed: Heats of formation of [2.2]paracyclophane-1-ene and [2.2]paracyclophane-1,9-diene - an experimental study. PubMed: Hydrolytic behavior of 5alpha-hydroxy-11beta- and 5beta-hydroxy-11alpha-substituted 19-norsteroids. PubMed: Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree. PubMed: Interspecific variation in terpenoid composition of defensive secretions of European Reticulitermes termites. PubMed: Regulation of floral scent production in petunia revealed by targeted metabolomics. PubMed: Aromadendrane transformations by Curvularia lunata ATCC 12017. PubMed: Identification of epoxyhenicosadiene and novel diepoxy derivatives as sex pheromone components of the clear-winged tussock moth Perina nuda. PubMed: The hetero-Diels-Alder addition of sulfur dioxide to 1-fluorobuta-1,3-dienes: the sofa conformations preferred by 6-fluorosultines (6-fluoro-3,6-dihydro-1,2-oxathiin-2-oxides) enjoy enthalpic and conformational Anomeric effects. PubMed: Structural and mechanistic studies on the activation and propagation of a cationic allylpalladium procatalyst in 1,6-diene cycloisomerization. PubMed: Sesquiterpenoid constituents of the liverworts Lepidozia fauriana and Lepidozia vitrea. PubMed: Correspondence of soldier defense secretion mixtures with cuticular hydrocarbon phenotypes for chemotaxonomy of the termite genus Reticulitermes in North America. PubMed: Two polycyclic compounds derived from a Diels-Alder reaction. PubMed: A practical large-scale synthesis of 17alpha-acetoxy-11beta-(4-N, N-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione (CDB-2914). PubMed: The steam volatile oil of Wollemia nobilis and its comparison with other members of the Araucariaceae (Agathis and Araucaria). PubMed: Progesterone, oestrogen and glucocorticoid receptors in the uterus and mammary glands of mares from mid- to late gestation. PubMed: Dienogest, a synthetic steroid, suppresses both embryonic and tumor-cell-induced angiogenesis. PubMed: Lignans and polyacetylenes from bupleurum acutifolium PubMed: The steroid promegestone is a noncompetitive antagonist of the Torpedo nicotinic acetylcholine receptor that interacts with the lipid-protein interface. PubMed: Germacrene C synthase from Lycopersicon esculentum cv. VFNT cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase. PubMed: 11 beta-substituted 13 beta-ethyl gonane derivatives exhibit reversal of antiprogestational activity. PubMed: Effects of two antiprogestins on early pregnancy in the long-tailed macaque (Macaca fascicularis). PubMed: Antisense to the glucocorticoid receptor in hippocampal dentate gyrus reduces immobility in forced swim test. PubMed: Steroid specificity of the human sperm membrane progesterone receptor. PubMed: Antioxidant: a new role for RU-486 and related compounds. PubMed: Synthesis of new 11 beta-substituted spirolactone derivatives. Relationship with affinity for mineralocorticoid and glucocorticoid receptors. PubMed: Reactions of vitamin E and its model compound 2,2,5,7,8-pentamethylchroman-6-ol with ozone. PubMed: Reversal of activity profile in analogs of the antiprogestin RU 486: effect of a 16 alpha-substituent on progestational (agonist) activity. PubMed: Effect of the progestagen R5020 (promegestone) and of progesterone on the uptake and on the transformation of estrone sulfate in the MCF-7 and T-47d human mammary cancer cells: correlation with progesterone receptor levels. PubMed: The effect of growth retardants on anthocyanin production in carrot cell suspension cultures. PubMed: ZK98299--a new antiprogesterone: biochemical characterization of steroid binding parameters in the calf uterine cytosol. PubMed: Synthesis of new 10 beta-propargylic and 11 beta-allenic steroidal spirolactones. PubMed: Demonstration of putative membrane and cytosol steroid receptors for 17α, 20β-dihydroxy-4-pregnen-3-one in brook troutSalvelinus fontinalis oocytes by photoaffinity labelling using synthetic progestin 17,21-dimethyl-19-nor-pregn-4,9-diene-3,20-dione (R5020). PubMed: Activation of thymocyte deoxyribonucleic acid degradation by endogenous glucocorticoids. PubMed: Progesterone action in normal mouse mammary gland. PubMed: Mechanism of action of a steroidal antiglucocorticoid in lymphoid cells. PubMed: Kinetic pulse-chase labeling study of the glucocorticoid receptor in mouse lymphoma cells. Effect of glucocorticoid and antiglucocorticoid hormones on intracellular receptor half-life. PubMed: Agonist-dependent phosphorylation and nuclear dephosphorylation of glucocorticoid receptors in intact cells. PubMed: The chemistry of 9 alpha-hydroxysteroids. 1. Preparation of 9 alpha,17 beta-dihydroxy-17 alpha-ethynylandrost-4-en-3-one. PubMed: Attenuation of preovulatory gonadotrophin surges by epostane: a new inhibitor of 3 beta-hydroxysteroid dehydrogenase. PubMed: Ligand-modulated regulation of progesterone receptor messenger ribonucleic acid and protein in human breast cancer cell lines. PubMed: RU486 is not an antiprogestin in the hamster. PubMed: Role of progesterone in the modulation of the preovulatory surge of gonadotropins and ovulation in the pregnant mare's serum gonadotropin-primed immature rat and the adult rat. PubMed: ORG-2058 as a ligand in the assay of progesterone receptor in breast cancer. PubMed: Abbreviation of the period of sexual behavior in female guinea pigs by the progesterone antagonist RU 486. PubMed: Antagonistic effect of glucocorticoids on retinoic acid induced growth inhibition and morphological alterations of a human cell line. PubMed: Modulation of lactogenic receptors by progestins in cultured human breast cancer cells. PubMed: Rapid in vivo effects of glucocorticoids on the integrity of rat lymphocyte genomic deoxyribonucleic acid. PubMed: A-ring conformational stability and progesterone-receptor binding affinity of 4-en-3-one steroids. PubMed: Zinc concentration and progestin receptor in human benign hyperplastic prostate. PubMed: High affinity binding of [3H]R5020 and [3H]progesterone by putative progesterone receptors in cytosol and nuclear extract of turtle oviduct. PubMed: Progestin binding in benign hyperplastic prostatic tissue. PubMed: Assessment of structural similarities in chick oviduct progesterone receptor subunits by partial proteolysis of photoaffinity-labeled proteins. PubMed: Estrogen and progesterone receptors in human uterus and oviduct. PubMed: Progestin receptors in ovaries of 4-day cycling rats. An autoradiographic study. PubMed: Presence of progesterone receptors and absence of oestrogen receptors in human intracranial meningioma cytosols. PubMed: Photoaffinity labeling of the chick progesterone receptor proteins. Similar hormone binding domains detected after removal of proteolytic interference. PubMed: Characterization of the cytosol androgen receptor of the human prostate. PubMed: Plant cell suspension cultures as model systems for investigating growth regulating compounds. PubMed: Progesterone receptors in mammary gland of the pregnant rat. PubMed: Comparative studies of aromatase inhibitors in cultured human breast cancer cells. PubMed: Hormone receptors of the baboon cardiovascular system. Biochemical characterization of aortic and myocardial cytoplasmic progesterone receptors. PubMed: Identification of a steroid receptor on the surface of Xenopus oocytes by photoaffinity labeling. PubMed: Photoaffinity labeling of glucocorticoid receptors. PubMed: Purification of a human progesterone receptor. PubMed: Direct inhibitory effect of glucocorticoids upon testicular luteinizing hormone receptor and steroidogenesis in vivo and in vitro. PubMed: Absence of high-affinity binding of progesterone (R 5020) in human placenta and fetal membranes. PubMed: Hormones modulate the concentration of cytoplasmic progestin receptors in the brain of male ring doves (Streptopelia risoria). PubMed: Binding of medroxyprogesterone acetate in human breast cancer. PubMed: Progestin receptors in rat brain: distribution and properties of cytoplasmic progestin-binding sites. PubMed: Progesterone "receptor" in rat ovary. PubMed: Assay of progesterone receptor binding sites with 17,21-dimethyl-19-norpregna-4,9-diene-3,20-dione and 16alpha-ethyl-21-hydroxy-19-nor-4-pregnene-3,20-dione as the radioactive ligands [proceedings]. PubMed: [Specific binding of 3H-progesterone to a plasma protein in the guinea pig fetus]. PubMed: Interaction of progestins with steroid receptors in human uterus. PubMed: Comparison of [3H]progesterone and [6,7-3H]-17,21-dimethyl-19-norpregna-4,9-diene-3,20-dione for the measurement of progesterone receptors in human malignant tissue. PubMed: Progestin binding in testes from three siblings with the syndrome of male pseudohermaphroditism with testicular feminization. PubMed: Characterization of unoccupied (R) and occupied (RA) androgen binding components of the hyperplastic human prostate. PubMed: Characterization and assay of the progesterone receptor in rat uterine cytosol. PubMed: Progestin binding sites in the rat hypothalamus pituitary and uterus. PubMed: N-(4-Acetamidophenyl)-anti-tricyclo [4.2.2.025-] deca-3, 9-diene-7, 8-endodicarboximide (1)--a chemically novel anticonvulsant. PubMed: Characterization and assay of progesterone receptor in human mammary carcinoma. PubMed: Specific progesterone receptors in dimethylbenzanthracene (DMBA)-induced mammary tumors.