parkeol
lanost-9(11)-en-3 beta-ol
 
Notes:
None found
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CAS Number: 514-45-4Picture of molecule3D/inchi
Nikkaji Web: J13.992K
XlogP3-AA: 9.20 (est)
Molecular Weight: 426.72770000
Formula: C30 H50 O
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 2.034e-005 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 parkeol usage levels up to:
 not for fragrance use.
 
Recommendation for parkeol 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 : 12313974
National Institute of Allergy and Infectious Diseases: Data
 (3S,5R,8S,10S,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,8,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
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References:
 (3S,5R,8S,10S,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,8,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 12313974
Pubchem (cas): 514-45-4
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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): C19918
HMDB (The Human Metabolome Database): HMDB35128
FooDB: FDB013763
VCF-Online: VCF Volatile Compounds in Food
Wikipedia: View
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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
 butyrospermum parkii seed
Search Trop  Picture
 vitellaria paradoxa stem bark
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Synonyms:
 lanost-9(11)-en-3 beta-ol
(3S,5R,8S,10S,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,8,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
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Articles:
PubMed: Identification of key amino acid residues determining product specificity of 2,3-oxidosqualene cyclase in Oryza species.
PubMed: Deficiency of a triterpene pathway results in humidity-sensitive genic male sterility in rice.
PubMed: Control of the 1,2-rearrangement process by oxidosqualene cyclases during triterpene biosynthesis.
PubMed: Catalytic mechanism and product specificity of oxidosqualene-lanosterol cyclase: a QM/MM study.
PubMed: Protein engineering of Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase into parkeol synthase.
PubMed: Divergent evolution of oxidosqualene cyclases in plants.
PubMed: Triterpene cyclases from Oryza sativa L.: cycloartenol, parkeol and achilleol B synthases.
PubMed: Triterpene alcohol and fatty acid composition of shea nuts from seven African countries.
PubMed: Protostadienol synthase from Aspergillus fumigatus: functional conversion into lanosterol synthase.
PubMed: Formation of triterpenoids throughout Olea europaea fruit ontogeny.
PubMed: Site-saturated mutagenesis of histidine 234 of Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase demonstrates dual functions in cyclization and rearrangement reactions.
PubMed: Tryptophan 232 within oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae influences rearrangement and deprotonation but not cyclization reactions.
PubMed: Plant lanosterol synthase: divergence of the sterol and triterpene biosynthetic pathways in eukaryotes.
PubMed: Phylogenetic and biochemical evidence for sterol synthesis in the bacterium Gemmata obscuriglobus.
PubMed: Directed evolution experiments reveal mutations at cycloartenol synthase residue His477 that dramatically alter catalysis.
PubMed: Oxidosqualene Cyclase Residues that Promote Formation of Cycloartenol, Lanosterol, and Parkeol We are grateful to Bridget M. Joubert for advice regarding mutagenesis. We thank Elizabeth A. Hart for an authentic parkeol standard, and for chromatographic and spectroscopic information. This research was funded by the National Institutes of Health (grant no. AI 41598) and the Robert A. Welch Foundation (grant no. C-1323). M.M.M. was an American Society of Pharmacognosy Undergraduate Fellow. M.J.R.S. was a Robert A. Welch Fellow and was supported by an NIH Biotechnology Training Grant (grant no. T32 GM08362).
PubMed: Steric bulk at cycloartenol synthase position 481 influences cyclization and deprotonation.
PubMed: In vivo and in vitro biosynthesis of saponins in sea cucumbers.
PubMed: Biosynthetic studies of marine lipids. 42. Biosynthesis of steroid and triterpenoid metabolites in the sea cucumber Eupentacta fraudatrix.
PubMed: Sterol biosynthesis via cycloartenol and other biochemical features related to photosynthetic phyla in the amoeba Naegleria lovaniensis and Naegleria gruberi.
PubMed: Biogenetic-type total synthesis. 24,25-Dihydrolanosterol, 24,25-dihydro- 13(17) -protosterol, isoeuphenol, (-)-isotirucallol, and parkeol.
PubMed: The conversion of parkeol into its 24,25-epoxide by tissue cultures of Nicotiana tabacum.
PubMed: [Synthesis of labeled tetracyclic triterpenes. I. Lanosterol, cycloartenol, parkeol and 31-norcycloartenol(25-14C) or (26,27-D). II. Lanosterol and cycloartenol (2-T)].
PubMed: Studies in phytosterol biosynthesis. Mechanism of biosynthesis of cycloartenol.
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