manoyl oxide
(3R- (3alpha,4abeta, 6aalpha,10abeta, 10balpha))-3-ethenyl dodecahydro-3,4a,7,7,10a-pentamethyl-1H-naphtho(2,1-b)pyran
None found
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CAS Number: 596-84-9Picture of molecule3D/inchi
Nikkaji Web: J148.810D
XlogP3-AA: 5.90 (est)
Molecular Weight: 290.49018000
Formula: C20 H34 O
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Google Scholar: with word "volatile"Search
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US Patents: Search
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Pubchem Patents: Search
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Physical Properties:
Assay: 90.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 338.00 to  339.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.000190 mmHg @ 25.00 °C. (est)
Flash Point: 311.00 °F. TCC ( 155.00 °C. )
logP (o/w): 6.887 (est)
Soluble in:
 water, 0.04131 mg/L @ 25 °C (est)
Insoluble in:
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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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 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
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 manoyl oxide usage levels up to:
 not for fragrance use.
Recommendation for manoyl oxide flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 6453839
National Institute of Allergy and Infectious Diseases: Data
Chemidplus: 0000596849
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NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 6453839
Pubchem (sid): 135192911
Pherobase: View
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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
HMDB (The Human Metabolome Database): Search
FooDB: FDB006376
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
None Found
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Potential Uses:
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Occurrence (nature, food, other): note
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(3R- (3alpha,4abeta, 6aalpha,10abeta, 10balpha))-3-ethenyl dodecahydro-3,4a,7,7,10a-pentamethyl-1H-naphtho(2,1-b)pyran
 manool oxide
(+)-manoyl oxide
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PubMed: Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare.
PubMed: Manoyloxide Sesterterpenoids from Salvia mirzayanii.
PubMed: Low-volatile lipophilic compounds in needles, defoliated twigs, and outer bark of Pinus thunbergii.
PubMed: Manoyl oxide (13R), the biosynthetic precursor of forskolin, is synthesized in specialized root cork cells in Coleus forskohlii.
PubMed: Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction.
PubMed: Extraction of essential oil from Cupressus sempervirens: comparison of global yields, chemical composition and antioxidant activity obtained by hydrodistillation and supercritical extraction.
PubMed: A diterpene synthase from the clary sage Salvia sclarea catalyzes the cyclization of geranylgeranyl diphosphate to (8R)-hydroxy-copalyl diphosphate.
PubMed: Identification of volatiles from Pinus silvestris attractive for Monochamus galloprovincialis using a SPME-GC/MS platform.
PubMed: A four-year naturalistic prospective study of cardiometabolic disease in antipsychotic-treated patients.
PubMed: Labdane diterpenoids and highly methoxylated bibenzyls from the liverwort Frullania inouei.
PubMed: Acylated manoyl oxide diterpenes of Stemodia trifoliata.
PubMed: Chemical composition of endemic Scorzonera sandrasica and studies on the antimicrobial activity against multiresistant bacteria.
PubMed: Growth inhibiting activity of volatile oil from Cistus creticus L. against Borrelia burgdorferi s.s. in vitro.
PubMed: Morphological, chemical and genetic differentiation of two subspecies of Cistus creticus L. (C. creticus subsp. eriocephalus and C. creticus subsp. corsicus).
PubMed: Assessment of some diterpenoids in commercial distilled gin.
PubMed: Antibacterial activity of labdane diterpenoids from Stemodia foliosa.
PubMed: Supercritical CO2 extract from needles of Pinus nigra ssp. laricio: combined analysis by GC, GC-MS and 13C NMR.
PubMed: Effect of the nature of the 3beta-substitution in manoyl oxides on the thermotropic behavior of DPPC lipid bilayer and on DPPC liposomes.
PubMed: Antileishmanial activity of natural diterpenes from Cistus sp. and semisynthetic derivatives thereof.
PubMed: ent-rosane and labdane diterpenoids from Sagittaria sagittifolia and their antibacterial activity against three oral pathogens.
PubMed: The effect of terpenoid extracts from 15 pine species on the feeding behavioural sequence of the late instars of the pine processionary caterpillar Thaumetopoea pityocampa.
PubMed: Manoyl oxide diterpenoids from Grindelia scorzonerifolia.
PubMed: Phaeoside, a novel galactoside of hydroxymanoyl oxide from the gibberellin A1-producing Phaeosphaeria sp. L487.
PubMed: Biotransformation of ent-13-epi-manoyl oxides difunctionalized at C-3 and C-12 by filamentous fungi.
PubMed: The biotransformation of the diterpene 2beta-hydroxy-ent-13-epi-manoyl oxide by Gibberella fujikuroi.
PubMed: A simple and rapid method for the differentiation of C-13 manoyl oxide epimers in biologically important samples using GC-MS analysis supported with NMR spectroscopy and computational chemistry results.
PubMed: Chemical studies of essential oils of Juniperus oxycedrus ssp. badia.
PubMed: Chemical analysis and antimicrobial activity of Halimium voldii.
PubMed: Manoyl oxide alpha-arabinopyranoside and grindelic acid diterpenoids from Grindelia integrifolia.
PubMed: New hemisynthetic manoyl oxide derivatives with antimicrobial activity.
PubMed: Labdane type diterpenes down-regulate the expression of c-Myc protein, but not of Bcl-2, in human leukemia T-cells undergoing apoptosis.
PubMed: Essential oils and hexane extracts from leaves and fruits of Cistus monspeliensis. Cytotoxic activity of ent-13-epi-manoyl oxide and its isomers.
PubMed: An interpopulation study of the essential oils of Cistus parviflorus L. growing in Crete (Greece).
PubMed: Five diterpenoids (agallochins A-E) from the mangrove plant Excoecaria agallocha Linn.
PubMed: Chemical analysis and antimicrobial studies on three species of Ferulago from Greece.
PubMed: Stereochemistry of the cyclization-rearrangement of (+)-copalyl diphosphate to (-)-abietadiene catalyzed by recombinant abietadiene synthase from Abies grandis.
PubMed: Analysis of labdane-type diterpenes from Cistus creticus (subsp. creticus and subsp. eriocephalus), by GC and GC-MS.
PubMed: Cytotoxic activity and antiproliferative effects of a new semi-synthetic derivative of Ent-3 beta-hydroxy-13-epi-manoyl oxide on human leukemic cell lines.
PubMed: Immunosuppressive diterpenoids from Tripterygium wilfordii.
PubMed: Composition and antibacterial activity of the essential oils of Stachys candida and S. chrysantha from southern Greece.
PubMed: Composition and antibacterial activity of the essential oils of Helichrysum rupestre and H. ambiguum growing in the Balearic Islands (Part III)
PubMed: Microbiological transformation of manoyl oxide derivatives by Mucor plumbeus.
PubMed: Composition and antimicrobial activity of the essential oil of Cistus creticus subsp. eriocephalus.
PubMed: Diterpenes from Solidago rugosa.
PubMed: Natural Metabolites of ent-13-epi-Manoyl Oxide and Other Cytotoxic Diterpenes from the Resin "LADANO" of Cistus creticus.
PubMed: Non-cytotoxic inhibition of macrophage eicosanoid biosynthesis and effects on leukocyte functions and reactive oxygen species of two novel anti-inflammatory plant diterpenoids.
PubMed: Chemical-microbiological synthesis of ent-13-epi-manoyl oxides with biological activities.
PubMed: Novel anti-inflammatory plant labdanes: comparison of in vitro properties with aspirin and indomethacin.
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