83036-62-8

Basic information

• Product Name: (1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate
• CAS NO: 83036-62-8
• Molecular Formula: C₃₄H₅₆O₆
• Molecular Weight: 560.8048
• Mol File: 83036-62-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 642.1°C at 760 mmHg
• Flash Point: 192.1°C
• Density: 1.12g/cm³
• Vapor Pressure: 3.39E-19mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: (1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate(83036-62-8)
• EPA Substance Registry System: (1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate(83036-62-8)

Safety Data

• Hazardous Substances Data: 83036-62-8(Hazardous Substances Data)

Usage

General Description

The chemical "(1aR,2S,5R,5aS,6S,8aS,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,3,4,5,5a,6,9,10,10a-decahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl tetradecanoate" is a complex organic compound consisting of a cyclopentane ring with a cyclopropyl group and a long chain ester appended. It contains multiple hydroxyl groups and a carbonyl group, as well as a tetradecanoate moiety. The compound has a highly rigid and unique structure due to the fused ring system, and the presence of the long chain ester suggests a role in lipid metabolism or storage. The specific stereochemistry and side chain composition imply potential biological activity and pharmacological properties. Further research and analysis are required to fully understand the function and potential applications of this compound.

Upstream product

• 30220-46-3 ingenol 
• 112-64-1 tetradecanoyl chloride 
• 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 
• 83036-74-2 ingenol-5β,20-O,O-isopropylidene-3β-O-myristinate 
• 143725-46-6 3-O-tetradecanoylingenol-20-aldehyde 

Relevant articles and documents

Total synthesis of natural derivatives and artificial analogs of 13-oxyingenol and their biological evaluation

We have established an efficient synthetic methodology for the 13-oxyingenol natural derivative (13-oxyingenol-13-dodecanoate-20-hexanoate), featuring a ring-closing olefin metathesis reaction for the “direct” construction of a highly strained inside-outside framework and a Mislow-Evans-type [2,3]-sigmatropic rearrangement for the stereoselective introduction of the hydroxy group at C5. We also synthesized artificial analogs of 13-oxyingenol and ingenol by using our synthetic strategy. In vitro activation assays of protein kinase C (PKC) α and δ revealed that the dodecanoyl group at O13 on 13-oxyingenol analogs had a significant role in PKCδ activation. The PKCα- or PKCδ-activating 13-oxyingenol and ingenol analogs induced both distinct morphological changes and increases of CD11b expression in HL-60 cells, which would be typical signs of HL-60 cell differentiation to macrophage-like cells, as expected by previous reports. Intriguingly, however, similar differentiation phenotypes were observed with the use of 13-oxyingenol natural derivatives and 13-oxyingenol-13-dodecanoate showing a remarkably less potent PKCα or PKCδ activation ability, which the PKC inhibitor G?6983 diminished. This indicated the involvement of other PKC isozymes or related kinase activities. 13-Oxyingenol analogs, which induced HL-60 cell differentiation, also induced HL-60 cell death, similar to the action of a phorbol ester, a strong PKC activator.

On the Chemistry of Ingenol, II. Esters of Ingenol and δ7,8-Isoingenol

Preparation and purification of 3-acylated of ingenol (1a) structurally related to naturally occuring, irritant and cocarcinogenic principles are described.It is shown that 3-acylated partly rearrange to corresponding 5-acylates when they are chromatograp