Showing Metabocard for 1-tetradecanoyl-2-(9Z)-octadecenoyl-sn-glycerol (BASm0005665)

Common Name

1-tetradecanoyl-2-(9z)-octadecenoyl-sn-glycerol

Description

DG(14:0/18:1(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(14:0/18:1(9Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of oleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the oleic acid moiety is 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

C₃₅H₆₆O₅

Average Mass

566.89550

Monoisotopic Mass

566.49103

IUPAC Name

(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (9Z)-octadec-9-enoate

Traditional Name

(2s)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (9z)-octadec-9-enoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC/C=C\CCCCCCCC(=O)O[C@@H](CO)COC(=O)CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C35H66O5/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(38)40-33(31-36)32-39-34(37)29-27-25-23-21-19-14-12-10-8-6-4-2/h16-17,33,36H,3-15,18-32H2,1-2H3/b17-16-/t33-/m0/s1

InChI Key

XEQQGHISHUGMIP-ASUORMEESA-N

CHEBI ID

CHEBI:75465

HMDB ID

HMDB0007015

Pathways

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

State

Not Available

Water Solubility

1.96e-05 g/l

logP

9.82

logS

-7.46

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

168.82 m³·mol⁻¹

Polarizability

73.46

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