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

CAS: 1617-70-5 C30 H48 O MW: 424.71176000

Identification

Namelupenone
IUPAC(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 Number1617-70-5
FDA UNIISearch
Molecular FormulaC30 H48 O
Molecular Weight424.71176000
MDL NumberMFCD03935405
Nikkaji NumberJ82.270A

Regulatory

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)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for lupenone usage levels up tonot for fragrance use.
Recommendation for lupenone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

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) 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).