EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

lupenone
lup-20(29)-en-3-one (8CI)(9CI)

Supplier Sponsors

Name:(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
CAS Number: 1617-70-5Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J82.270A
MDL:MFCD03935405
XlogP3-AA:9.60 (est)
Molecular Weight:424.71176000
Formula:C30 H48 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 485.70 °C. @ 760.00 mm Hg (est)
Flash Point: 395.00 °F. TCC ( 201.60 °C. ) (est)
logP (o/w): 10.400 (est)
Soluble in:
 water, 7.638e-005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Lupenone 0.985
Odor: characteristic
Use: Lupenone isolated from the roots of Pueraria thomsonii Benth. It effectively inhibited adipocyte differentiation through downregulating the related transcription factor, particularly the PPAR? gene.
ExtraSynthese
For experimental / research use only.
Lupenone (HPLC) ≥95%
Matrix Scientific
For experimental / research use only.
Lup-20(29)-en-3-one, 95+%
sds
Sigma-Aldrich: Aldrich
For experimental / research use only.
Lupenone
sds
 
Safety Information:
Preferred SDS: View
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for lupenone usage levels up to:
 not for fragrance use.
 
Recommendation for lupenone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :92158
National Institute of Allergy and Infectious Diseases:Data
(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
Chemidplus:0001617705
 
References:
 (1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):92158
Pubchem (sid):135048934
 
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
CHEMBL:View
KEGG (GenomeNet):C16990
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
 lup-20(29)-en-3-one (8CI)(9CI)
 

Articles:

PubMed:RP-HPLC characterization of lupenone and β-sitosterol in rhizoma musae and evaluation of the anti-diabetic activity of lupenone in diabetic Sprague-Dawley rats.
PubMed:Lupenone isolated from Adenophora triphylla var. japonica extract inhibits adipogenic differentiation through the downregulation of PPARγ in 3T3-L1 cells.
PubMed:Lupenone from Erica multiflora leaf extract stimulates melanogenesis in B16 murine melanoma cells through the inhibition of ERK1/2 activation.
PubMed:Synergistic Effect of Lupenone and Caryophyllene Oxide against Trypanosoma cruzi.
PubMed:Inhibition of protein tyrosine phosphatase 1B by lupeol and lupenone isolated from Sorbus commixta.
PubMed:The Willgerodt-Kindler reaction on lupenone: unusual oxidative dimerization.
PubMed:A new sesquiterpenoid from Scaphium macropodum (Miq.) Beumee.
PubMed:LUPENONE AND 18-ALPHA-OLEANAN-19-ALPHA-OL-3-ONE FROM SAMADERA INDICA.
PubMed:Chemical constituents of Anacolosa pervilleana and their antiviral activities.
PubMed:Isoboldine and lupenone from Neolitsea fuscata.
PubMed:[Triterpene compounds from Cirsium setosum].
PubMed:α-Amylase inhibitory triterpene from Abrus precatorius leaves.
PubMed:A new isocoumarin from Cajanus cajan (Fabaceae).
PubMed:Anti-inflammatory and antioxidant activities of constituents isolated from Pueraria lobata roots.
PubMed:Phytotoxic, antifungal activities and acute toxicity studies of the crude extract and compounds from Diospyros canaliculata.
PubMed:Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae).
PubMed:Chemical constituents of the bark of Dipteryx alata vogel, an active species against Bothrops jararacussu venom.
PubMed:Chemical constituents of the hemiparasitic plant Phoradendron brachystachyum DC Nutt (Viscaceae).
PubMed:[Studies on the triterpenoids constituents from Phyllodium elegans].
PubMed:Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD.
PubMed:Shamiminol: a new aromatic glycoside from the stem bark of Bombax ceiba.
PubMed:Bioactive constituents from Harpephyllum caffrum Bernh. and Rhus coriaria L.
PubMed:Lignans and other constituents from the roots of the Vietnamese medicinal plant Pseuderanthemum palatiferum.
PubMed:Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense.
PubMed:Chemical composition of French mimosa absolute oil.
PubMed:Chemical constituents of Piptadenia gonoacantha J.F. Macbr.
PubMed:Secondary plant substances in various extracts of the leaves, fruits, stem and bark of Caraipa densifolia Mart.
PubMed:Two new peltogynoids from Acacia nilotica Delile with kinase inhibitory activity.
PubMed:[Chemical constitutents of Bauhinia aurea].
PubMed:[Studies on constituents in herb of Senecio scandens].
PubMed:A new 3,4-seco-lupane derivative from Lasianthus gardneri.
PubMed:[Studies on chemical constituents of Liriope platyphylla].
PubMed:Preparative isolation and purification of chemical constituents from the root of Adenophora tetraphlla by high-speed counter-current chromatography with evaporative light scattering detection.
PubMed:Lipoxygenase inhibition by anadanthoflavone, a new flavonoid from the aerial parts of Anadenanthera colubrina.
PubMed:Evaluation of the antiviral and antimicrobial activities of triterpenes isolated from Euphorbia segetalis.
PubMed:In vitro evaluation of the cytotoxic and trypanocidal activities of Ampelozizyphus amazonicus (Rhamnaceae).
PubMed:Development of liquid chromatographic methods for the determination of phytosterols in Standard Reference Materials containing saw palmetto.
PubMed:Flavaglines and triterpenoids from the leaves of Aglaia forbesii.
PubMed:Pentacyclic triterpenes with selective bioactivity from Sebastiania adenophora leaves, Euphorbiaceae.
PubMed:Chemical study of triterpenoid resinous materials in archaeological findings by means of direct exposure electron ionisation mass spectrometry and gas chromatography/mass spectrometry.
PubMed:A new flavonol glycoside derivative from leaves of Moldenhawera nutans.
PubMed:A new triterpenoid ester from the fruits of Bruguiera parviflora.
PubMed:Cytotoxic constituents from Plumbago zeylanica.
PubMed:Characterization of archaeological frankincense by gas chromatography-mass spectrometry.
PubMed:Pentacyclic triterpenes from Euphorbia stygiana.
PubMed:Constituents of Acacia cedilloi and Acacia gaumeri. Revised structure and complete NMR assignments of resinone.
PubMed:Pentacyclic triterpenes from Chuquiraga ulicina.
PubMed:Cytotoxic constituents from the stems of Diospyros maritima.
PubMed:Two triterpenes lupanone and lupeol isolated and identified from Tamarindus indica linn.
PubMed:A new bisabolane sesquiterpenoid from Euphorbia chrysocoma.
PubMed:Unusual naphthoquinones, catechin and triterpene from Byrsonima microphylla.
PubMed:Cytotoxic activity of lupane-type triterpenes from Glochidion sphaerogynum and Glochidion eriocarpum two of which induce apoptosis.
PubMed:Cytotoxic lupane-type triterpenoids from Acacia mellifera.
PubMed:Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria.
PubMed:Antiplasmodial triterpenes from twigs of Gardenia saxatilis.
PubMed:Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase.
PubMed:A new oleanane glycoside from the stem bark of Albizia gummifera.
PubMed:A novel agarofuran sesquiterpene, celahin D from Celastrus hindsii Benth.
PubMed:Effect of the lipidosterolic extract of Serenoa repens (Permixon) and its major components on basic fibroblast growth factor-induced proliferation of cultures of human prostate biopsies.
PubMed:[Chemical studies of Strobilanthes cusia].
PubMed:[Studies on the chemical constituents of Desmodium styracifolium (Osbeck) Merr].
PubMed:Constituents of Shashen (Adenophora axilliflora).
 
Notes:
None found
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