60514-48-9

Basic information

• Product Name: 1,2-DIOCTANOYL-SN-GLYCEROL
• Synonyms: (S)-GLYCEROL 1,2-DIOCTANOATE;SN-1,2-DIOCTANOYLGLYCEROL;D-ALPHA,BETA-DICAPRYLIN;DOTAP;DOG;1,2-BIS(O-OCTANOYL)-SN-GLYCEROL;1,2-DICAPROYL-SN-GLYCEROL;1,2-DICAPRYLOYL-SN-GLYCEROL
• CAS NO: 60514-48-9
• Molecular Formula: C₁₉H₃₆O₅
• Molecular Weight: 344.49
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Protein Kinase Inhibitors and Activators
• Mol File: 60514-48-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 429.1 °C at 760 mmHg
• Flash Point: 136.8 °C
• Appearance: yellow/oil
• Density: 0.992 g/cm³
• Vapor Pressure: 3.65E-09mmHg at 25°C
• Refractive Index: 1.46
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• PKA: 13.70±0.10(Predicted)
• Stability: Temperature Sensitive
• CAS DataBase Reference: 1,2-DIOCTANOYL-SN-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIOCTANOYL-SN-GLYCEROL(60514-48-9)
• EPA Substance Registry System: 1,2-DIOCTANOYL-SN-GLYCEROL(60514-48-9)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• RTECS: RH0764500
• F: 10-21
• Hazardous Substances Data: 60514-48-9(Hazardous Substances Data)

Usage

Description

1,2-Dioctanoyl-sn-glycerol is a cell permeable lipid that functions as an analog of the PKC-activating second messenger Diacylglycerol (DAG). It has the ability to mimic the effects of tumor-promoting phorbol diesters on mitogenesis and EGF binding and action in intact cells. This unique property makes it a valuable compound in various applications across different industries.

Uses

Used in Pharmaceutical Industry:
1,2-Dioctanoyl-sn-glycerol is used as a research tool for studying the effects of DAG on cellular processes, particularly in the context of signal transduction and the activation of Protein Kinase C (PKC). Its ability to mimic the effects of tumor-promoting phorbol diesters makes it a valuable compound for understanding the underlying mechanisms of cell growth, proliferation, and differentiation.
Used in Reproductive Biology Research:
1,2-Dioctanoyl-sn-glycerol is used as an inducer of the acrosome reaction in human sperm, a critical process for fertilization. It has been found to be nearly equipotent with 1,2-dioleoyl-sn-glycerol in this regard, making it a useful compound for studying the mechanisms of sperm capacitation and the acrosome reaction, which are essential for successful fertilization.
Used in Cancer Research:
1,2-Dioctanoyl-sn-glycerol is used as a cell permeable lipid to investigate the role of DAG in the regulation of cell growth and proliferation, particularly in the context of cancer. Its ability to mimic the effects of tumor-promoting phorbol diesters allows researchers to study the signaling pathways and molecular mechanisms involved in cancer development and progression, potentially leading to the discovery of novel therapeutic targets and strategies for cancer treatment.

InChI:InChI=1/C19H36O5/c1-3-5-7-9-11-13-18(21)23-16-17(15-20)24-19(22)14-12-10-8-6-4-2/h17,20H,3-16H2,1-2H3/t17-/m0/s1

Upstream product

• 688021-88-7 1,2-di-O-octanoyl-3-O-benzyl-sn-glycerol 
• 111-64-8 n-octanoic acid chloride 

Downstream Products

• 19191-91-4 Dioctanoylphosphatidylcholine 
• 1044742-30-4 C₆₁H₇₇O₁₅P 
• 603136-85-2 octanoic acid 2-[(4,5-dimethoxy-2-nitro-benzyloxy)-(9H-fluoren-9-ylmethoxy)-phosphoryloxy]-1-octanoyloxymethyl-ethyl ester 
• 603136-89-6 Octanoic acid (R)-2-[(4,5-dimethoxy-2-nitro-benzyloxy)-hydroxy-phosphoryloxy]-1-octanoyloxymethyl-ethyl ester 
• 905911-92-4 2-O-benzyl-1,3-bis[(1,2-di-O-octanoyl-sn-glycero-3)-phosphoryl]glycerol di(2-cyanoethyl) ester 
• 163563-71-1 1,2-Di-O-octanoyl-sn-glycerol benzyl (N,N-diisopropylamino)phosphoramidite 

Relevant articles and documents

Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism

The stereochemistry of glycerophospholipids (GPLs) has been of interest for its roles in the evolution of life and in their biological activity. However, because of their structural complexity, no convenient method to determine their configuration has been reported. In this work, through the first systematic application of vibrational circular dichroism (VCD) spectroscopy to various diacylated GPLs, we have revealed that their chirality can be assigned by the sign of a VCD exciton couplet generated by the interaction of two carbonyl groups. This paper also presents spectroscopic evidence for the stereochemistry of GPLs isolated from bacteria, eukaryotes, and mitochondria.

Synthesis of short and long chain cardiolipins

A phosphoramidite approach using 2-cyanoethyl N,N-diisopropylchlorophosphoramidite was utilized for the first time to synthesize short chain cardiolipins. The approach was extended to synthesize long chain and their ether analogue. Optically active 1,2-di

Cosmetic composition

A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamine derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.