1,2-Distearoyl-sn-glycero-3-phosphocholine

HCID 94190

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Basic information

CAS: 816-94-4
Standard SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC
InChIKey: NRJAVPSFFCBXDT-HUESYALOSA-N
Molecular formula: C44H88NO8P
Average molar mass: 790.1 g/mol
Monoisotopic mass: 789.62475576

Names & identifiers

Preferred name: 1,2-Distearoyl-sn-glycero-3-phosphocholine
IUPAC: [(2R)-2,3-di(octadecanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
English name: 1,2-Distearoyl-sn-glycero-3-phosphocholine
Molecular formula: C44H88NO8P
Molecular weight: 790.15

Names & synonyms

816-94-41,2-Distearoyl-sn-glycero-3-phosphocholineDSPCDistearoyl phosphatidylcholinePC(18:0/18:0)1,2-Distearoyl-sn-3-phosphacholine043IPI2M0KL-DISTEAROYLLECITHINNSC-725285CHEBI:83718DTXSID20231218distearoyl-sn-glycero-3-phosphocholine

Show more names

1,2-Distearoyl-sn-glycero-3-PC(R)-2,3-Bis(stearoyloxy)propyl (2-(triMethylaMMonio)ethyl) phosphate1,2-Dioctadecanoyl-sn-glycero-3-phophocholine1,2-DIOCTADECANOYL-SN-GLYCERO-3-PHOSPHOCHOLINE18:0 PC1,2-DSPCDSPC(18:0)DSPC L-1118

1,2-DISTEARIN SN-3-PHOSPHORYLCHOLINEL-DSPCRefChem:906756DSPC R-1,2-distearoyllecithin, (R)-DTXCID20153709212-440-2PC(36:0)

Database identifiers

CAS: 816-94-4
PubChem CID: 94190
DTXSID: DTXSID20231218
ChEBI: CHEBI:83718
UNII: 043IPI2M0K
EC Number: 212-440-2
Nikkaji: J145.586I

Properties

Computed structural properties

XLogP: 15.6
Topological polar surface area: 111 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 8
Rotatable bonds: 44
Heavy atoms: 54
Formal charge: 0
Complexity: 888

Experimental & physicochemical properties

Physical DescriptionSolid

Collision Cross Section294.9 Å² [M+H]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]

Physicochemical properties

Melting point: 236 °C · 236°C(lit.)
storage temp.: -20 °C · -20°C
solubility: slightly sol. in Chloroform
form: powder to crystal
color: White to Almost white
biological source: semisynthetic
BRN: 3923978 · 3923978
Stability: Stable. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions: SKIN CONDITIONING
InChIKey: NRJAVPSFFCBXDT-HUESYALOSA-N
SMILES: [C@H](OC(=O)CCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCCCC |&1:0,r|
FDA UNII: 43 IPI2M0K · 043IPI2M0K
UNSPSC Code: 51191904 · 51191904
NACRES: 25 · NA.25
Symbol(GHS): 6 · GHS06,GHS08
Signal word: Danger
Hazard statements: 302 · H302-H315-H319-H331-H336-H351-H361d-H372-H412
Precautionary statements: 201 · P201-P273-P301+P312+P330-P302+P352-P304+P340+P311-P308+P313
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
F: 10 · 10-21
HS Code: 29232000 · 29232000
Storage Class: 13 · 13 - Non Combustible Solids

Safety & regulation

Safety data

F: 10-21
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29232000
Signal word: Danger
Symbol(GHS): GHS06,GHS08
safety_code: 22-24/25
Storage Class: 13 - Non Combustible Solids
Hazard statements: H302-H315-H319-H331-H336-H351-H361d-H372-H412
Precautionary statements: P201-P273-P301+P312+P330-P302+P352-P304+P340+P311-P308+P313

Chemistry & industry

Pharmacology

Tissue LocationsAll Tissues

Cellular LocationsExtracellular；Membrane

Metabolite PathwaysPhosphatidylcholine Biosynthesis PC(18:0/18:0)；Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)

Applications · 3 items

Description1,2-Distearoyl-sn-glycero-3-PC (DSPC) is a phospholipid containing the saturated long-chain (18:0) stearic acid inserted at the sn-1 and sn-2 positions. It is commonly used in the generation of micelles, liposomes, and other types of artificial membranes.

Uses18:0 PC (DSPC) has been used:in the microbubble monolayer preparation for biomolecule delivery studies into protoplastsin the preparation of liposomes for immobilization studies in the generation of porphyrin-phospholipid (PoP) liposomes for irinotecan (IRT) and doxorubicin delivery

General Description1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC) is a phospholtidylcholine with alkyl chain comprising 18 carbons. It has phophatidylcholine head group and its structure is similar to 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine (DPPC).