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Cas Database

113973-38-9

113973-38-9

Identification

  • Product Name:Octanoic acid, 1-(hydroxymethyl)-1,2-ethanediyl ester, (R)-

  • CAS Number: 113973-38-9

  • EINECS:

  • Molecular Weight:344.492

  • Molecular Formula: C19H36O5

  • HS Code:

  • Mol File:113973-38-9.mol

Synonyms:

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 5 Articles be found

Enzymatic preparation of enantiomerically pure sn-2,3-diacylglycerols: A stereoselective ethanolysis approach

Piyatheerawong, Weera,Yamane, Tsuneo,Nakano, Hideo,Iwasaki, Yugo

, p. 603 - 607 (2006)

Stereoselective ethanolysis of monoacid TAG by immobilized Rhizomucor miehei lipase (RML) was studied for preparation of optically pure sn-2,3-DAC. Trioctanoylglycerol (TO) was used as a model substrate. The enantiomeric purity of the product, sn-2,3-dioctanoylglycerol (sn-2,3-DO), was very high (percent enantiomeric excess > 99%) when an excess of ethanol was used. The result indicated that RML was highly stereosRMLelective toward the sn-1 position of TO under conditions of excess ethanol. The stereoselectivity of RML depended on the amount of ethanol. The larger the amount of ethanol was, the higher the stereoselectivity became. After optimizing the parameters such as reactant molar ratio, water content, and temperature, (ethanol/TO molar ratio = 31:1 and water content = 7.5 wt% of the reactants at 25°C), optically pure sn-2,3-DO was obtained at 61.1 mol% in the glyceride fraction in 20 min. The above conditions were further applied for ethanolysis of monoacid TAG with different acyl groups such as tridecanoylglycerol (C10:0), tridodecanoylglycerol (C12:0), tritetradecanoylglycerol (C14:0) and trioctadecenoylglycerol [triolein, (C18:1)]. The yields and enantiomeric purities of 1,2(2,3)-DAG were dramatically reduced when TAG with FA longer than decanoic acid were used. Copyright

Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism

Taniguchi, Tohru,Manai, Daisuke,Shibata, Masataka,Itabashi, Yutaka,Monde, Kenji

, p. 12191 - 12194 (2015/10/12)

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

Durgam, Gangadhar G.,Tsukahara, Ryoko,Makarova, Natalia,Walker, Michelle D.,Fujiwara, Yuko,Pigg, Kathryn R.,Baker, Daniel L.,Sardar, Vineet M.,Parrill, Abby L.,Tigyi, Gabor,Miller, Duane D.

, p. 633 - 640 (2007/10/03)

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

Acetal phosphate-derived LPA mimics, PPARgamma activators, and autotaxin inhibitors

-

Page/Page column 7; sheet 5, (2010/11/24)

Disclosed are compositions that modulate the effects of extracellular LPA receptors, the intracellular PPARγ receptor, and autotaxin, and methods for their use.

Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives

Chen, Jian,Feng, Li,Prestwich, Glenn D.

, p. 6511 - 6522 (2007/10/03)

New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsPn derivatives with diacylglyceryl moieties of different chain lengths.

Process route upstream and downstream products

Process route

Octanoic acid (R)-1-benzyloxymethyl-2-octanoyloxy-ethyl ester
876348-25-3

Octanoic acid (R)-1-benzyloxymethyl-2-octanoyloxy-ethyl ester

sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; In methanol;
95%
With hydrogen; Pd/C; In methanol;
95%
Octanoic acid (R)-2-(4-methoxy-benzyloxy)-1-octanoyloxymethyl-ethyl ester
214068-80-1

Octanoic acid (R)-2-(4-methoxy-benzyloxy)-1-octanoyloxymethyl-ethyl ester

sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Conditions
Conditions Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 3h; Ambient temperature;
80%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃;
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 70 percent / pyridine / CH2Cl2
2: 95 percent / H2 / Pd-C / methanol
With pyridine; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: pyridine / 4 h / 20 °C
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 20 °C
With pyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
tricaprilin
538-23-8

tricaprilin

glycerin monocaprylate
4228-48-2

glycerin monocaprylate

sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Conditions
Conditions Yield
With ethanol; immobilized Rhizomucor miehei lipase; at 25 ℃; for 0.333333h;
dibenzyl N,N-diisopropylphosphoroamidate
124575-22-0

dibenzyl N,N-diisopropylphosphoroamidate

sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Octanoic acid (S)-2-(bis-benzyloxy-phosphoryloxy)-1-octanoyloxymethyl-ethyl ester
876348-20-8

Octanoic acid (S)-2-(bis-benzyloxy-phosphoryloxy)-1-octanoyloxymethyl-ethyl ester

Conditions
Conditions Yield
dibenzyl N,N-diisopropylphosphoroamidate; sn-2,3-dioctanoylglycerol; With 1H-tetrazole; In dichloromethane;
With dihydrogen peroxide; In dichloromethane; water;
60%
(benzyloxy)chloro(diisopropylamino)phosphane
128753-68-4

(benzyloxy)chloro(diisopropylamino)phosphane

sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Octanoic acid (S)-2-(benzyloxy-diisopropylamino-phosphanyloxy)-1-octanoyloxymethyl-ethyl ester
214068-96-9

Octanoic acid (S)-2-(benzyloxy-diisopropylamino-phosphanyloxy)-1-octanoyloxymethyl-ethyl ester

Conditions
Conditions Yield
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h;
89%
phenyl phosphorodichloridite
3426-89-9

phenyl phosphorodichloridite

sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Octanoic acid (S)-2-(chloro-phenoxy-phosphanyloxy)-1-octanoyloxymethyl-ethyl ester
899827-23-7

Octanoic acid (S)-2-(chloro-phenoxy-phosphanyloxy)-1-octanoyloxymethyl-ethyl ester

Conditions
Conditions Yield
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -25 ℃; for 0.5h;
sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Octanoic acid (S)-1-octanoyloxymethyl-2-{phenoxy-[(1R,2R,3S,4R,5S,6S)-2,4,6-tris-benzyloxy-3-(diphenoxy-phosphoryloxy)-5-hydroxy-cyclohexyloxy]-phosphoryloxy}-ethyl ester

Octanoic acid (S)-1-octanoyloxymethyl-2-{phenoxy-[(1R,2R,3S,4R,5S,6S)-2,4,6-tris-benzyloxy-3-(diphenoxy-phosphoryloxy)-5-hydroxy-cyclohexyloxy]-phosphoryloxy}-ethyl ester

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: diisopropylethylamine / tetrahydrofuran / 0.5 h / -25 °C
2: tetrahydrofuran / 12 h / 20 °C
3: 0.540 g / aq. H2O2 / CH2Cl2 / 0.5 h
With dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Octanoic acid (S)-1-octanoyloxymethyl-2-{phenoxy-[(1R,2R,3S,4R,5S,6S)-2,4,6-tris-benzyloxy-3-(diphenoxy-phosphoryloxy)-5-hydroxy-cyclohexyloxy]-phosphanyloxy}-ethyl ester

Octanoic acid (S)-1-octanoyloxymethyl-2-{phenoxy-[(1R,2R,3S,4R,5S,6S)-2,4,6-tris-benzyloxy-3-(diphenoxy-phosphoryloxy)-5-hydroxy-cyclohexyloxy]-phosphanyloxy}-ethyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: diisopropylethylamine / tetrahydrofuran / 0.5 h / -25 °C
2: tetrahydrofuran / 12 h / 20 °C
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
Dibenzyl N,N-diisopropylphosphoramidite
108549-23-1

Dibenzyl N,N-diisopropylphosphoramidite

sn-2,3-dioctanoylglycerol
113973-38-9

sn-2,3-dioctanoylglycerol

Octanoic acid (S)-2-(bis-benzyloxy-phosphanyloxy)-1-octanoyloxymethyl-ethyl ester

Octanoic acid (S)-2-(bis-benzyloxy-phosphanyloxy)-1-octanoyloxymethyl-ethyl ester

Conditions
Conditions Yield
With 1H-tetrazole; In dichloromethane;
With 1H-tetrazole; In dichloromethane; at 23 ℃;

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