77573-45-6

Basic information

• Product Name: (1aR,7bR)-1aα,2,7aα,13,14,14aα-Hexahydro-1,1,6,6,9,9,11,13α-octamethyl-10aαH-2α,12aα-methano-1H,4H-cyclopropa[5,6][1,3]dioxolo[2',3']cyclopenta[1',2':9,10]cyclodeca[1,2-d][1,3]dioxin-15-ol
• Synonyms: (1aR,7bR)-1aα,2,7aα,13,14,14aα-Hexahydro-1,1,6,6,9,9,11,13α-octamethyl-10aαH-2α,12aα-methano-1H,4H-cyclopropa[5,6][1,3]dioxolo[2',3']cyclopenta[1',2':9,10]cyclodeca[1,2-d][1,3]dioxin-15-ol
• CAS NO: 77573-45-6
• Molecular Formula: C26H38O5
• Molecular Weight: 430.57692
• Mol File: 77573-45-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1aR,7bR)-1aα,2,7aα,13,14,14aα-Hexahydro-1,1,6,6,9,9,11,13α-octamethyl-10aαH-2α,12aα-methano-1H,4H-cyclopropa[5,6][1,3]dioxolo[2',3']cyclopenta[1',2':9,10]cyclodeca[1,2-d][1,3]dioxin-15-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1aR,7bR)-1aα,2,7aα,13,14,14aα-Hexahydro-1,1,6,6,9,9,11,13α-octamethyl-10aαH-2α,12aα-methano-1H,4H-cyclopropa[5,6][1,3]dioxolo[2',3']cyclopenta[1',2':9,10]cyclodeca[1,2-d][1,3]dioxin-15-ol(77573-45-6)
• EPA Substance Registry System: (1aR,7bR)-1aα,2,7aα,13,14,14aα-Hexahydro-1,1,6,6,9,9,11,13α-octamethyl-10aαH-2α,12aα-methano-1H,4H-cyclopropa[5,6][1,3]dioxolo[2',3']cyclopenta[1',2':9,10]cyclodeca[1,2-d][1,3]dioxin-15-ol(77573-45-6)

Safety Data

• Hazardous Substances Data: 77573-45-6(Hazardous Substances Data)

Upstream product

• 77573-43-4 (6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one 
• 137958-70-4 (9S)-9-deoxo-9-hydroxyingenol-5,20-acetonide 
• 67-64-1 acetone 
• 77573-44-5 ingenol-3,4:5,20-diacetonide 

Relevant articles and documents

On the Chemistry of Ingenol, IV Ingenol from Seeds of Euphorbia lathyris L. and Preparation of (9R)-9-Deoxo-9-hydroxyingenol with some Corresponding 3- and 9-Esters

A simple and fast procedure was worked out to prepare from the commercially available seeds of Euphorbia lathyris L. substantial amounts of the polyfunctional tetracyclic diterpene ingenol (1a).Ingenol-3,4:5,20-diacetonide (1d) was treated with five different bases at two different temperatures to achieve epimerization to 8-epiingenol.In any case unchanged 1d was obtained.By reduction of ingenol-3,4:5,20-diacetonide (1d) with sodium in ether/2-propanol (9R)-9-deoxo-9-hydroxyingenol-3,4:5,20-diacetonide (2b) was obtained and converted to the corresponding 5,20-monoacetonide 2e.Reduction of ingenol-5,20-acetonide (1e) with LiAlH4 in t etrahydrofuran furnished the epimeric (9S)-9-deoxo-9-hydroxyingenol-5,20-acetonide (3c).The (9R)-monoacetonide 2e was used to prepare the 3-tetradecanoate 2c of (9R)-9-deoxo-9-hydroxyingenol (2a).From the (9S)-monoacetonide 3c four 3-esters of (9S)-9-deoxo-9-hydroxyingenol (3a) were synthesized.The 3,4:5,20-diacetonides of 2a and 3a, i.e. 2b/3b were used to provide the 9-hexadecanoates 2f and 3j.The irritant activities of the 3-esters of the (9S)-series depend strongly on the nature of the acyl group, thus furnishing, e.g. the moderately irritant tetradecanoate 3e as well as the highly active benzoate 3g of 3a.The (9R)-3-tetradecanoate 2c exhibits comparable activity as its (9S)-analogue 3e.Thus, the spatial orientation (R or S) of the 9-hydroxy function plays a significant but not a crucial role for irritant activity.Both epimeric (9R/9S)-hexadecanoates 2f/3j were non irritant. Keywords: Conditional Cancerogens, Tumor Promoters, Skin Irritants, Ingenol, Structure-Bioactivity Relationships