| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-12-06 08:50:26 -0700 |
| Update Date |
2013-02-08 17:14:10 -0700 |
| HMDB ID |
HMDB05453 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso] |
| Description |
TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) or Triolein is a monoacid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides. TGs are fatty acid triesters of glycerol and may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) (with the help of lipases and bile secretions), which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org). TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- (9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-Octadecenoate
- (9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-Octadecenoic acid
- (9Z)-1,2,3-propanetriyl ester 9-Octadecenoate
- (9Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid
- (Z)-1,2,3-propanetriyl ester 9-Octadecenoate
- (Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid
- 1,2,3-Tri-(9Z-octadecenoyl)-sn-glycerol
- Actor LO 1
- Aldo TO
- Edenor NHTi-G
- Emerest 2423
- Emery 2423
- Emery oleic acid ester 2230
- Estol 1433
- Glycerin trioleate
- Glycerol trioleate
- Glycerol triolein
- Glyceryl trioleate
- Glyceryl-1,2,3-trioleate
- Kaolube 190
- Kemester 1000
- Oleic acid triglyceride
- Oleic triglyceride
- Oleyl triglyceride
- Radia 7363
- Raoline
- Sn-Glyceryl trioleate
- TG(18:1(9Z)/18:1(9Z)/18:1(9Z))
- Tri-Olein
- Triglyceride OOO
- Triolein
- Trioleoylglyceride
- Trioleoylglycerol
|
| Chemical Formula |
C57H104O6 |
| Average Molecular Weight |
885.4321 |
| Monoisotopic Molecular Weight |
884.78329106 |
| IUPAC Name |
1,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate |
| Traditional IUPAC Name |
triolein |
| CAS Registry Number |
122-32-7 |
| SMILES |
CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC |
| InChI Identifier |
InChI=1S/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25-,29-26-,30-27- |
| InChI Key |
PHYFQTYBJUILEZ-IUPFWZBJSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerolipids |
| Sub Class |
Triacylglycerols |
| Other Descriptors |
- Aliphatic Acyclic Compounds
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| Substituents |
- Acyclic Alkene
- Carboxylic Acid Ester
- Fatty Acid Ester
- Tricarboxylic Acid Derivative
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| Direct Parent |
Triacylglycerols |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane component
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
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| Physical Properties |
|---|
| State |
Liquid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
-32 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
Not Available
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| Tissue Location |
Not Available
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| Pathways |
Not Available
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| Normal Concentrations |
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|
Not Available |
| Abnormal Concentrations |
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|
Not Available |
Predicted Concentrations
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|
| Blood |
28.3768418 +/- 7.043489286 uM |
Adult (>18 years old) |
Both |
Normal (Most Probable) |
Calculated using MetaboAnalyst
|
| Blood |
175.3888889 +/- 30.28590309 uM |
Adult (>18 years old) |
Both |
Normal (Upper Limit) |
Calculated using MetaboAnalyst
|
|
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB002910 |
| KNApSAcK ID |
C00032423  |
| Chemspider ID |
4593733 |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Triolein |
| NuGOwiki Link |
HMDB05453 |
| Metagene Link |
HMDB05453 |
| METLIN ID |
4947 |
| PubChem Compound |
5497163 |
| PDB ID |
Not Available |
| ChEBI ID |
53753 |
| References |
|---|
| Synthesis Reference |
Desnuelle, P.; Naudet, M. Isomerization of oleic acid during the synthesis of triolein. Bull. soc. chim. (1945), 12 998-1001. CAN 40:19192 AN 1946:19192 CAPLUS |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
Not Available |
