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PC(18:1(9Z)/18:1(9Z)) (PC000320)

Record Information
Version1.0
Creation date2015-10-09 22:29:51 UTC
Update date2017-01-19 02:36:19 UTC
FoodComEx IDPC000320
FoodDB RecordFDB022133
Chemical Information
NamePC(18:1(9Z)/18:1(9Z))
DescriptionPC(18:1(9Z)/18:1(9Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:1(9Z)/18:1(9Z)), 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. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dioleoylphosphatidylcholine is found in human platelets and red blood cells, in mitochondria from skeletal muscle, lung, umbilical artery and vein endothelial cells (PMID: 15351277, 7138900, 2351875, 4046747, 2755318). While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. [HMDB]
CAS Number68737-67-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(Z,Z)-(1)-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-aheptacos-18-enyl)trimethylammonium 4-oxideHMDB
(Z,Z)-(1)-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxidehmdb
(Z,Z)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxo-9-octadecenyl)oxy]-3,5,9-trioxa-4-aheptacos-18-en-1-aminium 4-oxide hydroxide inner saltHMDB
(Z,Z)-4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxo-9-octadecenyl)oxy]-3,5,9-Trioxa-4-phosphaheptacos-18-en-1-aminium 4-oxide hydroxide inner salthmdb
1,2-Dioleoyl-rac-glycero-3-ocholineHMDB
1,2-dioleoyl-rac-glycero-3-phosphocholinehmdb
1,2-Dioleoylglycerol-3-orylcholineHMDB
1,2-Dioleoylglycerol-3-phosphorylcholinehmdb
1,2-Dioleoylglyceryl-3-orylcholineHMDB
1,2-Dioleoylglyceryl-3-phosphorylcholinehmdb
1,2-Dioleoyllechmdb
Atidylcholine(18:1/18:1)HMDB
Atidylcholine(18:1N9/18:1N9)HMDB
Atidylcholine(18:1W9/18:1W9)HMDB
Atidylcholine(36:2)HMDB
DioleoylatidylcholineHMDB
Dioleoylphosphatidylcholinehmdb
GPCho(18:1/18:1)HMDB
GPCho(18:1N9/18:1N9)HMDB
GPCho(18:1W9/18:1W9)HMDB
GPCho(36:2)HMDB
PC Aa C36:2HMDB
PC(18:1N9/18:1N9)HMDB
PC(18:1W9/18:1W9)HMDB
PC(36:2)HMDB
Chemical FormulaC44H84NO8P
IUPAC name[2-({2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono}oxy)ethyl]trimethylazanium
InChI IdentifierInChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3
InChI KeySNKAWJBJQDLSFF-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCC=CCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC
Average Molecular Weight786.1134
Monoisotopic Molecular Weight785.593455181
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 20 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available