20S,24R-Epoxydammar-12,25-diol-3-one

Base Information

Chemical Name:20S,24R-Epoxydammar-12,25-diol-3-one
CAS No.:25279-15-6
Molecular Formula:C₃₀H₅₀O₄
Molecular Weight:474.725
Hs Code.:
UNII:RCA3293YRJ
ChEMBL ID:CHEMBL2426028
Nikkaji Number:J129.884D
Mol file:25279-15-6.mol

Synonyms:3-Dehydropyxinol;25279-15-6;RCA3293YRJ;20S,24R-Epoxydammar-12,25-diol-3-one;UNII-RCA3293YRJ;(20S)-Protopanaxadiol metabolite M2-2;(20S,24R)-12beta,25-Dihydroxy-20,24-epoxydammaran-3-one;(12beta,24R)-20,24-Epoxy-12,25-dihydroxydammaran-3-one;Dammaran-3-one, 20,24-epoxy-12,25-dihydroxy-, (12beta,20S,24R)-;20S,24R-Epoxydammara-12beta,25-diol-3-one;CHEMBL2426028;(5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;AKOS027250676;FS-9658;(20S,24R)-12|A,25-Dihydroxy-20,24-epoxydammarane-3-one;(12.BETA.,24R)-20,24-EPOXY-12,25-DIHYDROXYDAMMARAN-3-ONE;(20S,24R)-12.BETA.,25-DIHYDROXY-20,24-EPOXYDAMMARAN-3-ONE;DAMMARAN-3-ONE, 20,24-EPOXY-12,25-DIHYDROXY-, (12.BETA.,20S,24R)-;(5R, 8R, 9R, 10R, 12R, 13R, 14R, 17S)-12-hydroxy-17-[(2S, 5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4, 4, 8, 10, 14-pentamethyl-1, 2, 5, 6, 7, 9, 11, 12, 13, 15, 16, 17-dodecahydrocyclopenta[a]phenanthren-3-one

Suppliers and Price of 20S,24R-Epoxydammar-12,25-diol-3-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Crysdot
Dammaran-3-one,20,24-epoxy-12,25-dihydroxy-,(12β,24R)- 95+%
5mg
$ 930.00

Arctom
20S,24R-Epoxydammar-12,25-diol-3-one
5mg
$ 593.00

Total 18 raw suppliers

Chemical Property of 20S,24R-Epoxydammar-12,25-diol-3-one

Chemical Property:

PSA：66.76000
LogP:5.92000
XLogP3:5.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:474.37091007
Heavy Atom Count:34
Complexity:864

Purity/Quality:

97% ^*data from raw suppliers

Dammaran-3-one,20,24-epoxy-12,25-dihydroxy-,(12β,24R)- 95+% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1(C2CCC3(C(C2(CCC1=O)C)CC(C4C3(CCC4C5(CCC(O5)C(C)(C)O)C)C)O)C)C
Isomeric SMILES:C[C@]1(CC[C@@H](O1)C(C)(C)O)[C@H]2CC[C@@]3([C@@H]2[C@@H](C[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCC(=O)C5(C)C)C)C)O)C
General Description (20S,24R)-12β,25-Dihydroxy-20,24-epoxydammarane-3-one (also known as 3-dehydropyxinol) is a dammarane-type triterpenoid derivative of pyxinol, which serves as a key scaffold for anti-inflammatory drug development due to its modifiable C-3 position and stereochemistry-dependent bioactivity. It exhibits potential in inhibiting pro-inflammatory mediators like NO, TNF-α, and IL-6 via the NF-κB pathway, with derivatives such as 3-oximinopyxinol showing efficacy comparable to steroid drugs. Additionally, its structural framework has been explored in ocotillol-type derivatives for modulating P-glycoprotein-mediated multidrug resistance in cancer therapy, highlighting its versatility in medicinal chemistry.

Technology Process of 20S,24R-Epoxydammar-12,25-diol-3-one

There total 8 articles about 20S,24R-Epoxydammar-12,25-diol-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

: 162062-88-6
(20S,24R)-epoxydammarane–3β,12β,25-triol

: 25279-15-6
(20S,24R)-epoxydammarane–12β,25-diol-3-one

Guidance literature:: With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 15h; Cooling with ice;

Reference yield:

: 6892-79-1,7755-01-3,30636-90-9,38243-15-1,53368-76-6,103834-30-6
protopanaxadiol

: 25279-15-6
(20S,24R)-epoxydammarane–12β,25-diol-3-one

Guidance literature:: Multi-step reaction with 4 steps

1: dmap; pyridine / 24 h / 20 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / -3 °C

3: potassium hydroxide; methanol / 2 h / Reflux

4: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C

With pyridine; methanol; dmap; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; potassium hydroxide; In dichloromethane;
DOI:10.1016/j.ejmech.2013.07.041

Reference yield:

: 7755-02-4
3,12-di-O-acetydammar-24-ene-3β,12β,20(S)-triol

: 25279-15-6
(20S,24R)-epoxydammarane–12β,25-diol-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / -3 °C

2: potassium hydroxide; methanol / 2 h / Reflux

3: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C

With methanol; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; potassium hydroxide; In dichloromethane;
DOI:10.1016/j.ejmech.2013.07.041