5822-57-1

Basic information

• Product Name: (3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• Synonyms: (3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• CAS NO: 5822-57-1
• Molecular Formula: C₂₉H₄₂O₁₀
• Molecular Weight: 550.64
• Mol File: 5822-57-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 188-189 °C(Solv: methanol (67-56-1); water (7732-18-5))
• Boiling Point: 757.3°Cat760mmHg
• Flash Point: 247.1°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1.8E-26mmHg at 25°C
• Refractive Index: 1.622
• PKA: 13.04±0.70(Predicted)
• CAS DataBase Reference: (3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde(5822-57-1)
• EPA Substance Registry System: (3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde(5822-57-1)

Safety Data

• Hazardous Substances Data: 5822-57-1(Hazardous Substances Data)

Usage

General Description

The chemical compound "(3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde" is a complex steroid derivative with a cyclopenta[a]phenanthrene core structure. It contains multiple hydroxy groups, a furan ring, and an aldehyde functional group. The compound is a dodecahydro-cyclopenta[a]phenanthrene-10-carbaldehyde with substituents at the 3, 5, 10, 13, 14, and 17 positions. The stereochemistry of the molecule is specified by the S and R configurations at different chiral centers. The compound's structure suggests potential biological activity and may be of interest for medicinal or pharmaceutical applications.

InChI:InChI=1/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15?,17-,18+,19?,20?,22+,23?,24?,25-,26+,27-,28-,29-/m0/s1

Upstream product

• 69980-52-5 2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide 
• 66-28-4 strophanthidin 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 

Downstream Products

• 7044-33-9 convalloside 

Relevant articles and documents

Antiarol cinnamate and africanoside, a cinnamoyl triterpene and a hydroperoxy-cardenolide from the stem bark of antiaris africana

From the methanol extract of the stem bark of the African tree Antiaris africana Engler, two new bioactive metabolites were isolated, namely, the α-amyrin derivative 1β,11α-dihydroxy-3β-cinnamoyl-α- amyrin (antiarol cinnamate, 1) and a cardiac glycoside, 3β-O-(α-L- rhamnopyranosyl)-14β-hydroperoxy-5β-hydroxy-19-oxo-17β-card- 20(22)-enolide (africanoside, 2a), together with the known compounds-α- amyrin and its acetate, β-sitosterol and its 3-O-β-D-glucopyranoside, friedelin, ursolic and oleanolic acid, 19-norperiplogenin, strophanthidol, strophanthidinic acid, periplogenin (3a), 3-epiperiplogenin, strophanthidin (3b) and 3,3-dimethoxy-4-O-β-D-xylopyronosyl-ellagic acid. Their structures were established on the basis of their spectroscopic data and by chemical methods, while 3a was additionally confirmed by Xray crystal structure analysis. The aglycone moiety possessing a hydroperoxy group was found for the first time in cardenolides. Compounds 1 and 2a showed no activity against bacteria, fungi, and microalgae; however, the crude extract exhibited a high toxicity against Artemia salina and a selective antitumor activity against human tumor cell lines. Africanoside (2a) effected a concentration-dependent inhibition of tumor cell growth with a mean IC50 value of 5.3nM. Georg Thieme Verlag KG Stuttgart - New York.