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Catalog No.:AA00065M
102-62-5 | 3-Hydroxypropane-1,2-diyl diacetate
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  • Technical Information
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Technical Information
Catalog Number:
Chemical Name:
3-Hydroxypropane-1,2-diyl diacetate
CAS Number:
Molecular Formula:
Molecular Weight:
MDL Number:
(2-acetyloxy-3-hydroxypropyl) acetate
InChI Key:
NSC Number:
Computed Properties
Compound Is Canonicalized:
Covalently-Bonded Unit Count:
Defined Atom Stereocenter Count:
Defined Bond Stereocenter Count:
Exact Mass:
Formal Charge:
Heavy Atom Count:
Hydrogen Bond Acceptor Count:
Hydrogen Bond Donor Count:
Isotope Atom Count:
Molecular Weight:
Monoisotopic Mass:
Rotatable Bond Count:
Topological Polar Surface Area:
Undefined Atom Stereocenter Count:
Undefined Bond Stereocenter Count:

Glyceryl diacetate 
Acetin, di- 
(Hydroxymethyl)ethylene acetate 
Acetin, 1,2-di- 
Glycerin diacetate 
Glycerine diacetate 
1,2,3-Propanetriol, 1,2-diacetate 
Acetic acid, diglyceride 
3-Hydroxypropane-1,2-diyl diacetate 
Estol 1582 
Estol 1583 
Glycerol 1,3-di(acetate) 
NSC 2348 
EINECS 246-941-2 
BRN 1775840 
1-(acetyloxy)-3-hydroxypropan-2-yl acetate 
2-(Acetyloxy)-1-(hydroxymethyl)ethyl acetate 
CCRIS 9354 
CCRIS 9462 
Diacetyl glycerine 
Glycerol Diacetate 
Diacetin (Related) 
Diacetyl glycerine (Related) 
3-02-00-00331 (Beilstein Handbook Reference) 
(+/-)-Glycerol 1,2-diacetate 
1,3-Propanetriol, 1,2-diacetate 
Glycerol diacetate 
(2-acetoxy-3-hydroxy-propyl) acetate 
(2-acetyloxy-3-hydroxypropyl) acetate 
Glycerol 1,2-diacetate 
Diacetin (contains Mono-, Tri-, Glycerol) 
2-(Acetyloxy)-1-(hydroxymethyl)ethyl acetate, AldrichCPR 
Glycerol Alpha,Alpha-Diacetate 
Glycerol 1, 3- di(acetate) 
1-Hydroxypropane-1,3-diyl diacetate compound with 3-hydroxypropane-1,2-diyl diacetate 
1,2,3-Propanetriol, diacetate 

Title: Synthesis, biological, and biophysical studies of DAG-indololactones designed as selective activators of RasGRP.

Journal: Bioorganic & medicinal chemistry 20140615

Title: Distinctive roles of PLD signaling elicited by oxidative stress in synaptic endings from adult and aged rats.

Journal: Biochimica et biophysica acta 20121201

Title: Glycidol exposure evaluation of humans who have ingested diacylglycerol oil containing glycidol fatty acid esters using hemoglobin adducts.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20121101

Title: A mechanism underlying the effects of polyunsaturated fatty acids on breast cancer.

Journal: International journal of molecular medicine 20120901

Title: Assessment of intracellular Ca2+, cAMP and 1,2-diacylglycerol in cryopreserved buffalo (Bubalus bubalis) spermatozoa on supplementation of taurine and trehalose in the extender.

Journal: Reproduction in domestic animals = Zuchthygiene 20120801

Title: Regulation of hippocampal long-term potentiation and long-term depression by diacylglycerol kinase ζ.

Journal: Hippocampus 20120501

Title: Development of diacyltetrol lipids as activators for the C1 domain of protein kinase C.

Journal: Molecular bioSystems 20120401

Title: A self-limiting regulation of vasoconstrictor-activated TRPC3/C6/C7 channels coupled to PI(4,5)P₂-diacylglycerol signalling.

Journal: The Journal of physiology 20120301

Title: Impact of DAG stimulation on mineral synthesis, mineral structure and osteogenic differentiation of human cord blood stem cells.

Journal: Stem cell research 20120301

Title: Dietary effects of pure and diacylglycerol-rich rice bran oil on growth pattern and lipid profile of rats.

Journal: Journal of oleo science 20120101

Title: Changes in the inositol lipid signal system and effects on the secretion of TNF-α by macrophages in severely scalded mice.

Journal: Burns : journal of the International Society for Burn Injuries 20111201

Title: Metabolic link between phosphatidylethanolamine and triacylglycerol metabolism in the yeast Saccharomyces cerevisiae.

Journal: Biochimica et biophysica acta 20111201

Title: N-methyl-substituted fluorescent DAG-indololactone isomers exhibit dramatic differences in membrane interactions and biological activity.

Journal: Chembiochem : a European journal of chemical biology 20111017

Title: Identification and quantitation of reaction intermediates and residuals in lipase-catalyzed transesterified oils by HPLC.

Journal: Applied biochemistry and biotechnology 20110901

Title: Hepatic steatosis by dietary-conjugated linoleic acid is accompanied by accumulation of diacylglycerol and increased membrane-associated protein kinase C ε in mice.

Journal: Molecular nutrition & food research 20110701

Title: Study of arachidonoyl specificity in two enzymes of the PI cycle.

Journal: Journal of molecular biology 20110603

Title: Hydrolysis of triacetin catalyzed by immobilized lipases: effect of the immobilization protocol and experimental conditions on diacetin yield.

Journal: Enzyme and microbial technology 20110506

Title: Effects of weight loss and exercise on insulin resistance, and intramyocellular triacylglycerol, diacylglycerol and ceramide.

Journal: Diabetologia 20110501

Title: The effects of long- or medium-chain fat diets on glucose tolerance and myocellular content of lipid intermediates in rats.

Journal: Obesity (Silver Spring, Md.) 20110401

Title: Imaging the early stages of phospholipase C/sphingomyelinase activity on vesicles containing coexisting ordered-disordered and gel-fluid domains.

Journal: Journal of lipid research 20110401

Title: High-resolution, imaging TOF-SIMS: novel applications in medical research.

Journal: Analytical and bioanalytical chemistry 20110301

Title: Diacyl glycerol arginine-based surfactants: biological and physicochemical properties of catanionic formulations.

Journal: Amino acids 20110201

Title: Protein kinase C isoforms: mediators of reactive lipid metabolites in the development of insulin resistance.

Journal: FEBS letters 20110121

Title: Pharmacological modulation of diacylglycerol-sensitive TRPC3/6/7 channels.

Journal: Current pharmaceutical biotechnology 20110101

Title: Metabolism and synthesis of lipids in the polyunsaturated fatty acid-producing fungus Mortierella alliacea.

Journal: Journal of oleo science 20110101

Title: Paradoxical increase in TAG and DAG content parallel the insulin sensitizing effect of unilateral DGAT1 overexpression in rat skeletal muscle.

Journal: PloS one 20110101

Title: Reversal of redox-dependent inhibition of diacylglycerol kinase by antioxidants in mesangial cells exposed to high glucose.

Journal: Molecular medicine reports 20110101

Title: Aluminium ions inhibit the formation of diacylglycerol generated by phosphatidylcholine-hydrolysing phospholipase C in tobacco cells.

Journal: The New phytologist 20101001

Title: Sprouty proteins inhibit receptor-mediated activation of phosphatidylinositol-specific phospholipase C.

Journal: Molecular biology of the cell 20101001

Title: Phospholipase C activity affinity purifies with the Torpedo nicotinic acetylcholine receptor.

Journal: The Journal of biological chemistry 20100402

Title: Ca2+ influx and protein scaffolding via TRPC3 sustain PKCbeta and ERK activation in B cells.

Journal: Journal of cell science 20100315

Title: End-products diacylglycerol and ceramide modulate membrane fusion induced by a phospholipase C/sphingomyelinase from Pseudomonas aeruginosa.

Journal: Biochimica et biophysica acta 20100101

Title: Continuous measurement of galactolipid hydrolysis by pancreatic lipolytic enzymes using the pH-stat technique and a medium chain monogalactosyl diglyceride as substrate.

Journal: Biochimica et biophysica acta 20091001

Title: CalDAG-GEFI is at the nexus of calcium-dependent platelet activation.

Journal: Blood 20090917

Title: Anionic nucleotide--lipids for in vitro DNA transfection.

Journal: Bioconjugate chemistry 20090901

Title: Hydrogen peroxide is a second messenger in phase 2 enzyme induction by cancer chemopreventive dithiolethiones.

Journal: Chemical research in toxicology 20090817

Title: Age-related changes in the metabolization of phosphatidic acid in rat cerebral cortex synaptosomes.

Journal: Archives of biochemistry and biophysics 20090815

Title: OX40-OX40 ligand interaction may activate phospholipase C signal transduction pathway in human umbilical vein endothelial cells.

Journal: Chemico-biological interactions 20090814

Title: Insulin action on polyunsaturated phosphatidic acid formation in rat brain: an 'in vitro' model with synaptic endings from cerebral cortex and hippocampus.

Journal: Neurochemical research 20090701

Title: Lipid compounds of the umbilical cord artery and their alterations in preeclampsia.

Journal: Atherosclerosis 20090601

Title: Conformationally constrained analogues of diacylglycerol (DAG). 31. Modulation of the biological properties of diacylgycerol lactones (DAG-lactones) containing rigid-rod acyl groups separated from the core lactone by spacer units of different lengths.

Journal: Journal of medicinal chemistry 20090528

Title: Differential regulation of threonine and tyrosine phosphorylations on protein kinase Cdelta by G-protein-mediated pathways in platelets.

Journal: The Biochemical journal 20090101

Title: A high oleic sunflower oil fatty acid esters of plant sterols mixed with dietary diacylglycerol reduces plasma insulin and body fat accumulation in Psammomys obesus.

Journal: Lipids in health and disease 20090101

Title: Role of estrogenic compounds (diethylstibestrol, 17beta-estradiol, and bisphenol A) in the phosphorylation of substrate by protein kinase Calpha.

Journal: Journal of biochemical and molecular toxicology 20090101

Title: Spatiotemporal dynamics of lipid signaling: protein kinase C as a paradigm.

Journal: IUBMB life 20081201

Title: Regulation of diacylglycerol production and protein kinase C stimulation during sperm- and PLCzeta-mediated mouse egg activation.

Journal: Biology of the cell 20081101

Title: In vitro effects of phosphatidylcholine and transgalactooligosaccharides on the production of 1,2-sn-diacylglycerol by Bifidobacterium longum biovar infantis.

Journal: Journal of applied microbiology 20081101

Title: Korean red ginseng attenuates hypercholesterolemia-enhanced platelet aggregation through suppression of diacylglycerol liberation in high-cholesterol-diet-fed rabbits.

Journal: Phytotherapy research : PTR 20080601

Title: The mood stabilizer valproate inhibits both inositol- and diacylglycerol-signaling pathways in Caenorhabditis elegans.

Journal: Molecular biology of the cell 20080501

Title: High-performance liquid chromatographic assay with ultraviolet spectrometric detection for the evaluation of inhibitors of phosphatidylinositol-specific phospholipase C.

Journal: Analytical biochemistry 20080415

Title: Atf2 transcription factor binds to the APP1 promoter in Cryptococcus neoformans: stimulatory effect of diacylglycerol.

Journal: Eukaryotic cell 20080201

Title: Direct activation of transient receptor potential vanilloid 1(TRPV1) by diacylglycerol (DAG).

Journal: Molecular pain 20080101

Title: Properties, regulation, and in vivo functions of a novel protein kinase D: Caenorhabditis elegans DKF-2 links diacylglycerol second messenger to the regulation of stress responses and life span.

Journal: The Journal of biological chemistry 20071026

Title: A processive lipid glycosyltransferase in the small human pathogen Mycoplasma pneumoniae: involvement in host immune response.

Journal: Molecular microbiology 20070901

Title: Full CD3/TCR activation through cholesterol-depleted lipid rafts.

Journal: Cellular signalling 20070701

Title: Functional analysis of a lipid galactosyltransferase synthesizing the major envelope lipid in the Lyme disease spirochete Borrelia burgdorferi.

Journal: FEMS microbiology letters 20070701

Title: Respective hydrolysis and esterification of esterified and free plant stanols occur rapidly in human intestine after their duodenal infusion in triacyl- or diacylglycerol.

Journal: Lipids 20070701

Title: Possible enhancing activity of diacylglycerol on 4-nitroquinoline 1-oxide induced carcinogenesis of the tongue in human c-Ha-ras proto-oncogene transgenic rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20070601

Title: Effect of tricyclodecan-9-yl potassium xanthate (D609) on phospholipid metabolism and cell death during oxygen-glucose deprivation in PC12 cells.

Journal: Neuroscience 20070525

Title: [RasGRP proteins--Ras-activating factors].

Journal: Postepy biochemii 20070101

Title: Study of changes in diacylglycerol content on nerve excitation.

Journal: Biochemistry. Biokhimiia 20061001

Title: Signaling pathway of morphine induced acute thermal hyperalgesia in mice.

Journal: Pain 20060801

Title: Combined therapy with PPARalpha agonist and L-carnitine rescues lipotoxic cardiomyopathy due to systemic carnitine deficiency.

Journal: Cardiovascular research 20060601

Title: Evidence that phospholipase-C-dependent, calcium-independent mechanisms are required for directional migration of T-lymphocytes in response to the CCR4 ligands CCL17 and CCL22.

Journal: Journal of leukocyte biology 20060601

Title: Dissociation of regulated trafficking of TRPC3 channels to the plasma membrane from their activation by phospholipase C.

Journal: The Journal of biological chemistry 20060428

Title: Effect of diacylglycerol on the development of impaired glucose tolerance in sucrose-fed rats.

Journal: Lipids 20060401

Title: Emerging roles of phosphatidylinositol 3-monophosphate as a dynamic lipid second messenger.

Journal: Archives of physiology and biochemistry 20060101

Title: The EP3 receptor stimulates ceramide and diacylglycerol release and inhibits growth of primary keratinocytes.

Journal: Experimental dermatology 20051201

Title: Effect of cholecystokinin octapeptide on diacylglycerol-PKC signaling pathway in rat pulmonary interstitial macrophages stimulated by lipopolysaccharide.

Journal: Acta pharmacologica Sinica 20051201

Title: Identification of an inactivating cysteine switch in protein kinase Cepsilon, a rational target for the design of protein kinase Cepsilon-inhibitory cancer therapeutics.

Journal: Cancer research 20051115

Title: Domain exchange between human toll-like receptors 1 and 6 reveals a region required for lipopeptide discrimination.

Journal: The Journal of biological chemistry 20051104

Title: Dietary fish oil attenuates cardiac hypertrophy in lipotoxic cardiomyopathy due to systemic carnitine deficiency.

Journal: Cardiovascular research 20051101

Title: The origin of C1A-C2 interdomain interactions in protein kinase Calpha.

Journal: The Journal of biological chemistry 20051028

Title: Analysis of a novel diacylglycerol kinase from Dictyostelium discoideum: DGKA.

Journal: Biochemistry 20050802

Title: A novel diacylglycerol-lactone shows marked selectivity in vitro among C1 domains of protein kinase C (PKC) isoforms alpha and delta as well as selectivity for RasGRP compared with PKCalpha.

Journal: The Journal of biological chemistry 20050722

Title: Honokiol-induced neurite outgrowth promotion depends on activation of extracellular signal-regulated kinases (ERK1/2).

Journal: European journal of pharmacology 20050601

Title: Combined interaction of phospholipase C and apolipoprotein A-I with small unilamellar lecithin-cholesterol vesicles: influence of apolipoprotein A-I concentration and vesicle composition.

Journal: Biochemistry 20050517

Title: Amplification of Ca2+ signaling by diacylglycerol-mediated inositol 1,4,5-trisphosphate production.

Journal: The Journal of biological chemistry 20050325

Title: Sustained diacylglycerol accumulation resulting from prolonged G protein-coupled receptor agonist-induced phosphoinositide breakdown in hepatocytes.

Journal: Journal of cellular biochemistry 20050201

Title: Conformationally constrained analogues of diacylglycerol (DAG). 23. Hydrophobic ligand-protein interactions versus ligand-lipid interactions of DAG-lactones with protein kinase C (PK-C).

Journal: Journal of medicinal chemistry 20040923

Title: Phospholipase C gene expression, protein content, and activities in cardiac hypertrophy and heart failure due to volume overload.

Journal: American journal of physiology. Heart and circulatory physiology 20040801

Title: Conformationally constrained analogues of diacylglycerol. 24. Asymmetric synthesis of a chiral (R)-DAG-lactone template as a versatile precursor for highly functionalized DAG-lactones.

Journal: Organic letters 20040708

Title: Control of the CDPethanolamine pathway in mammalian cells: effect of CTP:phosphoethanolamine cytidylyltransferase overexpression and the amount of intracellular diacylglycerol.

Journal: The Biochemical journal 20040501

Title: Dietary conjugated linoleic acid increases the mRNA ratio of Bax/Bcl-2 in the colonic mucosa of rats.

Journal: The Journal of nutritional biochemistry 20040401

Title: Clostridium perfringens alpha-toxin activates the sphingomyelin metabolism system in sheep erythrocytes.

Journal: The Journal of biological chemistry 20040326

Title: Lipid transfer particle mediates the delivery of diacylglycerol from lipophorin to fat body in larval Manduca sexta.

Journal: Journal of lipid research 20040301

Title: Conformationally constrained analogues of diacylglycerol. 20. The search for an elusive binding site on protein kinase C through relocation of the carbonyl pharmacophore along the sn-1 side chain of 1,2-diacylglycerol lactones.

Journal: Journal of medicinal chemistry 20040129

Title: Phospholipase C, but not InsP3 or DAG, -dependent activation of the muscarinic receptor-operated cation current in guinea-pig ileal smooth muscle cells.

Journal: British journal of pharmacology 20040101

Title: Involvement of phosphatidylcholine hydrolysis by phospholipase C in prostaglandin F2alpha-induced 1,2-diacylglycerol formation in osteoblast-like MC3T3-E1 cells.

Journal: Journal of bone and mineral metabolism 20040101

Title: The diacylglycerol and protein kinase C pathways are not involved in insulin signalling in primary rat hepatocytes.

Journal: European journal of biochemistry 20031201

Title: Free fatty acids induce cell differentiation to infective forms in Trypanosoma cruzi.

Journal: The Biochemical journal 20031101

Title: Effect of CD40--CD40 ligand interaction on diacylglycerol-protein kinase C and inositol trisphosphate-Ca(2+) signal transduction pathway in human umbilical vein endothelial cells.

Journal: Clinica chimica acta; international journal of clinical chemistry 20031101

Title: Mitogenic effects of phospholipase D and phosphatidic acid in transiently permeabilized astrocytes: effects of ethanol.

Journal: Journal of neurochemistry 20031001

Title: Refolding from denatured inclusion bodies, purification to homogeneity and simplified assay of MGDG synthases from land plants.

Journal: Protein expression and purification 20030901

Title: Impact of alpha-tocopherol on cardiac hypertrophy due to energy metabolism disorder: the involvement of 1,2-diacylglycerol.

Journal: Cardiovascular research 20030601

Title: Synthesis and analysis of symmetrical and nonsymmetrical disaturated/monounsaturated triacylglycerols.

Journal: Journal of agricultural and food chemistry 20030326

Title: IGF-I-induced phosphorylation of connexin 43 by PKCgamma: regulation of gap junctions in rabbit lens epithelial cells.

Journal: Investigative ophthalmology & visual science 20030301

Title: Changes in distinct species of 1,2-diacylglycerol in cardiac hypertrophy due to energy metabolic disorder.

Journal: Cardiovascular research 20030101

Title: S-carboxymethylcysteine inhibits neutrophil activation mediated by N-formyl-methionyl-leucyl-phenylalanine.

Journal: European journal of pharmacology 20020802

Title: Advanced glycation end-products induce apoptosis of bovine retinal pericytes in culture: involvement of diacylglycerol/ceramide production and oxidative stress induction.

Journal: Free radical biology & medicine 20020715

Title: Mechanism of angiotensin II-induced phospholipase D activation in bovine adrenal glomerulosa cells.

Journal: Molecular and cellular endocrinology 20020628

Title: Specificity of soluble phospholipid binding sites on human factor Xa.

Journal: Biochemistry 20020618

Title: Metabolic labelling of membrane microdomains/rafts in Jurkat cells indicates the presence of glycerophospholipids implicated in signal transduction by the CD3 T-cell receptor.

Journal: The Biochemical journal 20020501

Title: Determination of the diglyceride content in greek virgin olive oils and some commercial olive oils by employing (31)P NMR spectroscopy.

Journal: Journal of agricultural and food chemistry 20020410

Title: Dietary orotic acid increases 1 ,2-diacylglycerol level and lowers superoxide dismutase activity in rat liver.

Journal: Journal of nutritional science and vitaminology 20020201

Title: Protein kinase C changes in diabetes: is the concept relevant to neuropathy?

Journal: International review of neurobiology 20020101

Title: [A role of protein kinase C in signal reactions in outer segments of the bovine retinal rods].

Journal: Biofizika 20020101

Title: Orotic acid added to casein, but not to egg protein, soy protein, or wheat gluten diets increases 1,2-diacylglycerol levels and lowers superoxide dismutase activities in rat liver.

Journal: Bioscience, biotechnology, and biochemistry 20011001

Title: Effects of liposomes of different phospholipid composition on the induction of respiratory burst in human blood monocytes and alveolar macrophages.

Journal: Membrane & cell biology 20010701

Title: Low- and high-affinity phorbol ester and diglyceride interactions with protein kinase C: 1-O-alkyl-2-acyl-sn-glycerol enhances phorbol ester- and diacylglycerol-induced activity but alone does not induce activity.

Journal: Biochemistry 20010522

Title: Involvement of 1,2-diacylglycerol in improvement of heart function by etomoxir in diabetic rats.

Journal: Life sciences 20010216

Title: Modulation of inducible nitric oxide synthase expression in rat intestinal cells by colon tumor promoters.

Journal: International journal of oncology 20010101

Title: The inhibitory mechanism of rebamipide on the mediator release in the guinea pig lung mast cells activated with specific antigen-antibody reactions.

Journal: Pharmacology 20010101

Title: Protein kinase C control of gene expression.

Journal: Critical reviews in eukaryotic gene expression 20010101

Title: [Age features of glycerolipid metabolism in rat liver under short term exposure to thyroxine].

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20010101

Title: Effects of insulin and phospholipase C in control and denervated rat skeletal muscle.

Journal: The American journal of physiology 19910201

Title: Insulin-like growth factor-I stimulates diacylglycerol production via multiple pathways in Balb/c 3T3 cells.

Journal: The Journal of biological chemistry 19901005

Title: Alteration of 1,2-diacylglycerol content in myocardium from diabetic rats.

Journal: Diabetes 19880901

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