Showing Metabocard for 1,2-di-(9Z-octadecenoyl)-sn-glycerol (BASm0002447)

Common Name

1,2-di-(9z-octadecenoyl)-sn-glycerol

Description

DG(18:1(9Z)/18:1(9Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:1(9Z)/18:1(9Z)/0:0), in particular, consists of two chains of oleic acid at the C-1 and C-2 positions. The oleic acid moieties are derived from vegetable oils, especially olive and canola oil. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.

Structure

Molecular Formula

C₃₉H₇₂O₅

Average Mass

620.98600

Monoisotopic Mass

620.53798

IUPAC Name

(2S)-1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate

Traditional Name

1,2-dioleoyl-sn-glycerol

CAS Registry Number

Not Available

SMILES

CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC/C=C\CCCCCCCC

InChI Identifier

InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18-/t37-/m0/s1

InChI Key

AFSHUZFNMVJNKX-LLWMBOQKSA-N

CHEBI ID

CHEBI:52333

HMDB ID

HMDB0007218

Pathways

Name	SMPDB/PathBank
Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:0)
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:1(11Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:2(11Z,14Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:1(13Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:1(15Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:2(13Z,16Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))

State

Not Available

Water Solubility

1.25e-05 g/l

logP

10.26

logS

-7.70

pKa (Strongest Acidic)

14.58

pKa (Strongest Basic)

-2.98

Hydrogen Acceptor Count

Hydrogen Donor Count

Polar Surface Area

72.83 Å²

Rotatable Bond Count

Physiological Charge

Formal Charge

Refractivity

188.34 m³·mol⁻¹

Polarizability

80.99

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