(-)-abietadiene
(4aS,4bR,10aS)-7-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene
 
Notes:
None found
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CAS Number: 35241-40-8Picture of molecule3D/inchi
Nikkaji Web: J668.689C
Beilstein Number: 2504776
XlogP: 6.50 (est)
Molecular Weight: 272.47504000
Formula: C20 H32
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 360.32 °C. @ 760.00 mm Hg (est)
Flash Point: 324.00 °F. TCC ( 162.00 °C. ) (est)
logP (o/w): 8.509 (est)
Soluble in:
 water, 0.001371 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for (-)-abietadiene usage levels up to:
 not for fragrance use.
 
Recommendation for (-)-abietadiene flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 443470
National Institute of Allergy and Infectious Diseases: Data
 (4aS,4bR,10aS)-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene
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References:
 (4aS,4bR,10aS)-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 443470
Pubchem (sid): 14040
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
KEGG (GenomeNet): C11878
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 juniperus conva
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 juniperus procera
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Synonyms:
 abieta-7,13-diene
(-)-abieta-7,13-diene
 abieta-7(8),13(14)-diene
 phenanthrene, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,1,4a-trimethyl-7-(1-methylethyl)-, (4aS,4bR,10aS)-
(4aS,4bR,10aS)-7-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene
(4aS,4bR,10aS)-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene
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Articles:
PubMed: Essential oil composition of Ficus benjamina (Moraceae) and Irvingia barteri (Irvingiaceae).
PubMed: Evolution of conifer diterpene synthases: diterpene resin acid biosynthesis in lodgepole pine and jack pine involves monofunctional and bifunctional diterpene synthases.
PubMed: A single residue change leads to a hydroxylated product from the class II diterpene cyclization catalyzed by abietadiene synthase.
PubMed: Bifunctional cis-abienol synthase from Abies balsamea discovered by transcriptome sequencing and its implications for diterpenoid fragrance production.
PubMed: Insights into diterpene cyclization from structure of bifunctional abietadiene synthase from Abies grandis.
PubMed: [Research advances of diterpene synthase].
PubMed: Chemical composition of the essential oils of the berries of Juniperus oxycedrus L. ssp. rufescens (L. K.) and Juniperus oxycedrus L. ssp. macrocarpa (S. & m.) Ball. and their antioxidant activities.
PubMed: The need for enzymatic steering in abietic acid biosynthesis: gas-phase chemical dynamics simulations of carbocation rearrangements on a bifurcating potential energy surface.
PubMed: The primary diterpene synthase products of Picea abies levopimaradiene/abietadiene synthase (PaLAS) are epimers of a thermally unstable diterpenol.
PubMed: Seasonal variation, chemical composition, and analgesic and antimicrobial activities of the essential oil from leaves of Tetradenia riparia (Hochst.) Codd in southern Brazil.
PubMed: Immunofluorescence localization of levopimaradiene/abietadiene synthase in methyl jasmonate treated stems of Sitka spruce (Picea sitchensis) shows activation of diterpenoid biosynthesis in cortical and developing traumatic resin ducts.
PubMed: Antimicrobial and antiparasitic abietane diterpenoids from the roots of Clerodendrum eriophyllum.
PubMed: Diterpene cyclases and the nature of the isoprene fold.
PubMed: Laser microdissection of conifer stem tissues: isolation and analysis of high quality RNA, terpene synthase enzyme activity and terpenoid metabolites from resin ducts and cambial zone tissue of white spruce (Picea glauca).
PubMed: Redetermination and absolute configuration of 7α-hy-droxy-royleanone.
PubMed: Regulation of resin acid synthesis in Pinus densiflora by differential transcription of genes encoding multiple 1-deoxy-D-xylulose 5-phosphate synthase and 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase genes.
PubMed: Investigating the conservation pattern of a putative second terpene synthase divalent metal binding motif in plants.
PubMed: Antiparasitic, nematicidal and antifouling constituents from Juniperus berries.
PubMed: In vitro anti-inflammatory activity of larch (Larix decidua L.) sawdust.
PubMed: Functional plasticity of paralogous diterpene synthases involved in conifer defense.
PubMed: A single residue switch converts abietadiene synthase into a pimaradiene specific cyclase.
PubMed: Synergistic substrate inhibition of ent-copalyl diphosphate synthase: a potential feed-forward inhibition mechanism limiting gibberellin metabolism.
PubMed: Identification and functional analysis of bifunctional ent-kaurene synthase from the moss Physcomitrella patens.
PubMed: Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1).
PubMed: Wound-induced terpene synthase gene expression in Sitka spruce that exhibit resistance or susceptibility to attack by the white pine weevil.
PubMed: Metabolic flux analysis of diterpene biosynthesis pathway in rice.
PubMed: Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450 monooxygenase.
PubMed: Functional characterization of nine Norway Spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily.
PubMed: Bifunctional abietadiene synthase: mutual structural dependence of the active sites for protonation-initiated and ionization-initiated cyclizations.
PubMed: Mechanism of abietadiene synthase catalysis: stereochemistry and stabilization of the cryptic pimarenyl carbocation intermediates.
PubMed: Abietadiene synthase catalysis: conserved residues involved in protonation-initiated cyclization of geranylgeranyl diphosphate to (+)-copalyl diphosphate.
PubMed: Abietadiene synthase catalysis: mutational analysis of a prenyl diphosphate ionization-initiated cyclization and rearrangement.
PubMed: Bifunctional abietadiene synthase: free diffusive transfer of the (+)-copalyl diphosphate intermediate between two distinct active sites.
PubMed: Genomic organization of plant terpene synthases and molecular evolutionary implications.
PubMed: Abietadiene synthase from grand fir (Abies grandis): characterization and mechanism of action of the "pseudomature" recombinant enzyme.
PubMed: Stereochemistry of the cyclization-rearrangement of (+)-copalyl diphosphate to (-)-abietadiene catalyzed by recombinant abietadiene synthase from Abies grandis.
PubMed: Abietadiene synthase from grand fir (Abies grandis). cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase involved in resin acid biosynthesis.
PubMed: [Royleanones in the roots of Salvia officinalis L. of domestic provenance and their antimicrobial activity].
PubMed: A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis.
PubMed: Purification and characterization of taxa-4(5),11(12)-diene synthase from Pacific yew (Taxus brevifolia) that catalyzes the first committed step of taxol biosynthesis.
PubMed: An antimicrobial abietane from the root of Plectranthus hereroensis.
PubMed: Diterpenoid resin acid biosynthesis in conifers: enzymatic cyclization of geranylgeranyl pyrophosphate to abietadiene, the precursor of abietic acid.
PubMed: Diterpenoid resin acid biosynthesis in conifers: characterization of two cytochrome P450-dependent monooxygenases and an aldehyde dehydrogenase involved in abietic acid biosynthesis.
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