1617-70-5

Basic information

• Product Name: LUPENONE
• Synonyms: Aids-082905;-en-3-one;Lup-20(29);LUPENONE;18-LUPEN-3-ONE;LUPENONE(RG);5α-Lup-20(29)-en-3-one;Lup-20(29)-en-3-one
• CAS NO: 1617-70-5
• Molecular Formula: C30H48O
• Molecular Weight: 424.7
• Product Categories: Building block
• Mol File: 1617-70-5.mol

Chemical Properties

• Melting Point: 165-167°C
• Boiling Point: 485.7°Cat760mmHg
• Flash Point: 201.6°C
• Appearance: /
• Density: 0.973g/cm³
• Vapor Pressure: 1.38E-09mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: LUPENONE(CAS DataBase Reference)
• NIST Chemistry Reference: LUPENONE(1617-70-5)
• EPA Substance Registry System: LUPENONE(1617-70-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 1617-70-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Lupenone is used as a therapeutic agent for its antioxidant and anticholinesterase activities. Its antioxidant properties help protect cells from damage caused by reactive oxygen species, while its anticholinesterase activity can be beneficial in treating conditions related to the nervous system, such as Alzheimer's disease.
Additionally, as a potential PTP1B inhibitor, Lupenone may play a role in the development of new treatments for various diseases, including obesity and type 2 diabetes, where PTP1B inhibition has been shown to have positive effects on insulin sensitivity and glucose metabolism.
Used in Cosmetics Industry:
Lupenone's antioxidant properties also make it a valuable ingredient in the cosmetics industry. It can be used in skincare products to protect the skin from oxidative stress and environmental damage, promoting a healthier and more youthful appearance.
Used in Agricultural Applications:
In agriculture, Lupenone's antioxidant and anticholinesterase activities can be harnessed to develop natural pesticides or growth regulators that promote plant health and protect crops from pests and diseases without causing harm to the environment or human health.

InChI:InChI=1/C30H48O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-23,25H,1,9-18H2,2-8H3

Upstream product

• 545-47-1 lupenol 
• 6610-55-5 Glochidone 
• 79875-73-3 3,3-ethylenedioxylup-20⁽²⁹⁾-ene 
• 545-47-1 lupeol 
• 107596-77-0 lup-20⁽²⁹⁾-en-3-ol 
• 33869-84-0 3-epilupeol 
• 3607-91-8 lup-20⁽²⁹⁾-en-3-oxime 
• 6610-54-4 epi-lupenyl acetate 
• 473-98-3 betulin 
• 87001-74-9 Toluene-4-sulfonic acid (1R,3aS,5aR,5bR,9S,11aR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-3a-ylmethyl ester 
• 72944-06-0 30-hydroxylup-20⁽²⁹⁾-en-3-one 
• 79875-81-3 3,3-ethylenedioxylup-20⁽²⁹⁾-en-30-al 
• 79875-80-2 3,3-ethylenedioxylup-20⁽²⁹⁾-en-30-ol 

Downstream Products

• 1617-71-6 lupenone 2,4-dinitrophenylhydrazone 
• 545-47-1 lupenol 
• 1721-81-9 α-lupene 
• 3186-72-9 lupan-3-one 
• 472-15-1 Betulinic acid 
• 38736-77-5 3-epibetulinic acid 
• 51511-05-8 adiantulupanone 
• 1620005-01-7 C₃₆H₅₅NO 
• 1315246-27-5 C₄₃H₆₇N₃O₂ 
• 1315246-26-4 C₄₀H₆₂N₂O₃ 
• 1617-68-1 lupeol acetate 
• 72944-06-0 30-hydroxylup-20⁽²⁹⁾-en-3-one 

Related news

Novel access to epilupeol through chemoselective hydrogenation of LUPENONE (cas 1617-70-5) using platinum-based organotin catalysts07/19/2019

Catalytic hydrogenation of terpenes constitutes one of the most interesting reactions in the transformation of natural products. One of the key goals in this synthesis is the selective hydrogenation of the CO bond for obtaining biologically active epimeric alcohols. In the present work, the use ...detailed

Relevant articles and documents

3-Oxolup-20(29)-en-30-al, a New Lupane from Gymnosporia emarginata (Celastraceae)

The steam bark of Gymnosporia emarginata (Willd.) Hook f. ex.Thw. (Celastraceae) contains a number of triterpenes including a new oxygenated lupane, 3-oxolup-20(29)-en-30-al (1) and two related lupanes, 3β-hydroxylup-20(29)-en-30-al (2) and 30-hydroxylup-20(29)-en-3-one (3).The structures of these compounds have been established by spectroscopic and chemical methods.

Antidyslipidemic and antioxidant effects of novel lupeol-derived chalcones

A series of Lupeol-based chalcones have been synthesized aiming to enhance the therapeutic efficacy of parent compound, the novel compounds were evaluated for their antidyslipidemic activity in triton-WR 1339 induced hyperlipidemic rats. Among the ten synthesized chalcones, the most active K4, K8, and K9 reversed the plasma levels of TC by (24, 25, 27 %), phospholipid by (25, 26, 25 %) and triacylglycerol by (27, 24, 24 %) respectively. In addition, the compounds showed significant in vitro antioxidant activity. The lipid lowering activity of these compounds were mediated through lipoprotein lipase activation (12-21 %) and enhanced post-heparin lipolytic activity (15-16 %). The compounds also displayed noteworthy inhibitory effect on 3-hydroxy-3-methyl-glutaryl reductase activity (in vitro). The in vitro effect of the most active compounds on MDI-induced adipogenesis using 3T3-L1 preadipocytes at 10 and 20 μM concentrations showed significant inhibition (20-32 %) of adipogenesis.

Isolation of lupeol, design and synthesis of lupeol derivatives and their biological activity

The triterpenoid, lupeol (1) has been isolated from the leaves extract of Walsura trifoliate. Few novel derivatives (4a-j) were synthesized from the naturally occurring lupeol (1) and confirmed by spectroscopic methods, and tested for antimicrobial and anti-proliferative activity against MDAMB-231, IMR32and A549 cell lines. This all compound showed moderate activities.

A new 3,4-seco-lupane derivative from Lasianthus gardneri

A new seco-ring A lupane triterpene derivative (1), along with lupenone, lupeol, β-sitosterol, ursolic acid, and stigmasterol 3-O-β -D-glucoside, were isolated from a methanol extract of mature stems of Lasianthus gardneri, a shrub from the family Rubiaceae growing in Sri Lanka. The structure and stereochemistry of the new compound were determined using a combination of 13C and 1H homo- and heteronuclear 2D NMR experiments and from mass spectral data. The structure of 1 was confirmed by partial synthesis from lupeol.

Design and synthesis of new lupeol derivatives and their α-glucosidase inhibitory and cytotoxic activities

A series of lupeol derivatives 2, 2a-2f, 2a-2h, 3a-3e, and 4a-4b were designed, synthesised and evaluated for their α-glucosidase inhibitory and cytotoxic activities. Among synthetic derivatives, lupeol analogues 2b and 2e containing a benzylidene chain exhibited the best activity against α-glucosidase and superior to the positive agent with the IC50 values of 29.4 ± 1.33 and 20.1 ± 0.91 μM, respectively. Lupeol analogues 2d and 3a showed weak cytotoxicity against K562 cell line with the IC50 values of 76.6 ± 2.40 and 94.4 ± 1.51 μM, respectively.

Oxidation at C-16 enhances butyrylcholinesterase inhibition in lupane triterpenoids

A set of triterpenoids with different grades of oxidation in the lupane skeleton were prepared and evaluated as cholinesterase inhibitors. Allylic oxidation with selenium oxide and Jones's oxidation were employed to obtain mono-, di- and tri-oxolupanes, starting from calenduladiol (1) and lupeol (3). All the derivatives showed a selective inhibition of butyrylcholinesterase over acetylcholinesterase (BChE vs. AChE). A kinetic study proved that compounds 2 and 9, the more potent inhibitors of the series, act as competitive inhibitors. Molecular modeling was used to understand their interaction with BChE, the role of carbonyl at C-16 and the selectivity towards this enzyme over AChE. These results indicate that oxidation at C-16 of the lupane skeleton is a key transformation in order to improve the cholinesterase inhibition of these compounds.

Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors

A series of heterocyclic derivatives including indoles, pyrazines along with oximes and esters were synthesized from lupeol and evaluated for anti-inflammatory activity through inhibition of lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW 264.7 and J774A.1 cells. All the synthesized molecules of lupeol were found to be more active in inhibiting NO production with an IC50 of 18.4-48.7 μM in both the cell lines when compared to the specific nitric oxide synthase (NOS) inhibitor, L-NAME (IC50 = 69.21 and 73.18 μM on RAW 264.7 and J774A.1 cells, respectively). The halogen substitution at phenyl ring of indole moiety leads to potent inhibition of NO production with half maximal concentration ranging from 18.4 to 41.7 μM. Furthermore, alkyl (11, 12) and p-bromo/iodo (15, 16) substituted compounds at a concentration of 20 μg/mL exhibited mild inhibition (29-42%) of LPS-induced tumor necrosis factor alpha (TNF-α) and weak inhibition (10-22%) towards interleukin 1-beta (IL-1β) production in both the cell lines. All the derivatives were found to be non-cytotoxic when tested at their IC50 (μM). These findings suggest that the derivatives of lupeol could be a lead to potent inhibitors of NO.

Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD

Lupane triterpenoids 2 and 5-12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure-activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFT-calculated vibrational circular dichroism spectra. The CompareVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures.

Oxidative deprotection of oximes, phenylhydrazones and semicarbazones using pyridinium chlorochromate in catalytic amount with t-butyl hydroperoxide and in the solid state on montmorillonite K-10 clay support under microwave irradiation

Pyridinium chlorochromate (FCC) and other oxochromium(VI) reagents have been extensively employed in excess of the stoichiometric amount (2 equivalents or more) for efficient cleavage of oximes to carbonyl compounds. The aim of this study is to replace excess use of toxic chromium(VI) reagents and develop cleaner environment-friendly general methods of cleavage of imine derivatives such as oximes, phenylhydrazones and semicarbazones using PCC in catalytic or stoichiometric amount. Two approaches of greening the deprotection process with PCC are conceived of which the first one is based on the catalytic use of the reagent (0.1 equiv.) in combination with an excess of 70% t-butyl hydroperoxide as the cooxidant. Mild selective regeneration of carbonyl compounds from oximes, phenylhydrazones and semicarbazones has been accomplished in good-to-excellent yields (70-98%) by this method. With focus on rate enhancement coupled with efficiency of cleavage, an alternative microwave-assisted solid-state solventiess protocol of deprotection employing a stoichiometric amount of PCC dispersed on montmorillonite K-10 clay is also evaluated. It offers an expeditious efficient (74-98% yields) general route of cleavage of these procarbonyl compounds. Absence of overoxidation, particularly for oxidation-prone aryl aldehydes, is the key advantage of both these methods.