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

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

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

• 163563-71-1 1,2-Di-O-octanoyl-sn-glycerol benzyl (N,N-diisopropylamino)phosphoramidite 
• 905911-92-4 2-O-benzyl-1,3-bis[(1,2-di-O-octanoyl-sn-glycero-3)-phosphoryl]glycerol di(2-cyanoethyl) ester 
• 1044742-30-4 C₆₁H₇₇O₁₅P 
• 19191-91-4 Dioctanoylphosphatidylcholine 
• 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 

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.

A synthesis of dioctanoyl phosphatidylinositol

A synthesis of the naturally occurring enantiomer of phosphatidylinositol is reported. A resolution strategy, using camphor as a chiral auxiliary is employed to obtain the desired, enantiomerically pure, inositol derivative. Dioctanoyl lipid chains are appended to the molecule, which are shorter than the naturally occurring lipid chains, providing the molecule with enhanced water solubility.

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

Synthesis and pharmacological evaluation of second-generation phosphatidic acid derivatives as lysophosphatidic acid receptor ligands

Short-chain phosphatidic acid derivatives, dioctanoyl glycerol pyrophosphate (DGPP 8:0, 1) and phosphatidic acid 8:0 (PA 8:0, 2), were previously identified as subtype-selective LPA1 and LPA3 receptor antagonists. Recently, we report

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.

Cosmetic composition containing DOPA derivatives

A composition for topical application to human hair or skin contains a chemical analogue of dihydroxyphenyl alanine (DOPA). This chemical analogue can be absorbed by skin or by a hair follicle and metabolised in-vivo, thus leading to the formation of melanin in skin or to the growth of melanin-pigmented hair. Consequently the composition can give controlled skin darkening to mimic sun-induced tanning or can bring about the growth of dar hair in place of the grey or white hair.

Cosmetic composition

A composition suitable for topical application to mammalian skin or hair for inducing, maintaining or increasing hair growth comprises a glycosaminoglycanase inhibitor chosen from aldonomonolactones, alduronomonolactones and acylated monosaccharides, and a cosmetically acceptable vehicle for the inhibitor; the total amount of the inhibitor present in the composition being sufficient to increase hair growth in the rat, when said composition is applied topically thereto over a period of no more than 3 months, by at least 10% more than that obtainable using a control composition from which the said inhibitor has been omitted, in accordance with the Rat Hair Growth Test.

Cosmestic 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 glutamic acid 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.

Method of growing hair

A method for inducing, maintaining or increasing hair growth which is achieved by topically applying a preserved composition to mammalian skin and hair in a mammal having need thereof, the composition comprising a hexosaccharic acid, salts and esters thereof, in an amount sufficient to induce, maintain or increase hair growth.