manoyl oxide
(3R- (3alpha,4abeta, 6aalpha,10abeta, 10balpha))-3-ethenyl dodecahydro-3,4a,7,7,10a-pentamethyl-1H-naphtho(2,1-b)pyran
Identification
| Name | manoyl oxide |
| IUPAC | (3R,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromene |
| CAS Number | 596-84-9 |
| FDA UNII | Search |
| Molecular Formula | C20 H34 O |
| Molecular Weight | 290.49018000 |
| Nikkaji Number | J148.810D |
Regulatory
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 | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(13R)-8,13-
epoxylabd-14-ene
(3R- (3alpha,4abeta, 6aalpha,10abeta, 10balpha))-3-
ethenyl dodecahydro-3,4a,7,7,10a-pentamethyl-1H-naphtho(2,1-b)pyran
(3R,4aS,6aR,10aR,10bS)-3-
ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromene
manool oxide
(+)-
manoyl oxide
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.