35932-39-9

Basic information

• Product Name: 2-Hydroxymethylpropenoic acid dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester
• Synonyms: 2-Hydroxymethylpropenoic acid dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester;Saupirin;Saupirine
• CAS NO: 35932-39-9
• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.3744
• Mol File: 35932-39-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 566.2°Cat760mmHg
• Flash Point: 203.8°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 3.54E-15mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: 2-Hydroxymethylpropenoic acid dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxymethylpropenoic acid dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester(35932-39-9)
• EPA Substance Registry System: 2-Hydroxymethylpropenoic acid dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester(35932-39-9)

Safety Data

• Hazardous Substances Data: 35932-39-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2

Upstream product

• 859843-12-2 (5R)-2-hydroxymethyl-5-isopropenyl-cyclohex-2-enone 

Downstream Products

• 35932-46-8 deacylcynaropicrin 
• 71305-80-1 8α-acetoxyzaluzanin D 
• 68370-45-6 aguerin B 

Relevant articles and documents

Total synthesis of cynaropicrin

Cynaropicrin is found in artichoke (Cynara scolymus) and is the source of its bitter taste and it is a sesquiterpene lactone with a 5-7-5 tricyclic skeleton, six chiral centers, and fourexo-olefins. This natural product has numerous attractive biological activities including the inhibition of NF-κB activation, antihepatitis C activity, and antitrypanosomal activity. In this study, the first total synthesis of cynaropicrin was achieved starting from (S)-α-pinene. The synthesis involved a stereoselective Favorskii rearrangement and an indium-promoted diastereoselective Barbier reaction.

SESQUITERPENE LACTONES IN MONGOLIAN Saussurea lipshitzii

Five known guaianolides were isolated from the areal part of Saussurea lipshitzii (Asteraceae) collected in South Gobi, Mongolia: cynaropicrin (I), janerin (II), chlorojanerin (III), 15-deschloro-15-acetoxychlorojanerin (IV), and 15-deschloro-15-hydroxychlorojanerin (V).The correlation between I-V and the β-configuration of the C-4/C-15 bond in II-V was shown by biomimetic chemical transformations, suggesting compound I as the possible common precursor.