1,2-Dihexanoyl-sn-glycero-3-phosphocholine
Basic information
- CAS
34506-67-7- Standard SMILES
CCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCC- InChIKey
DVZARZBAWHITHR-GOSISDBHSA-N- Molecular formula
- C20H40NO8P
- Average molar mass
- 453.5 g/mol
- Monoisotopic mass
- 453.24915423
Overview
1,2-dihexanoyl-sn-glycero-3-phosphocholine is a phosphatidylcholine 12:0 in which both acyl groups are specified as hexanoyl. It has a role as a surfactant. It is functionally related to a hexanoic acid.
Names & identifiers
- Preferred name
- 1,2-Dihexanoyl-sn-glycero-3-phosphocholine
- IUPAC
- [(2R)-2,3-di(hexanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
- English name
- 1,2-Dihexanoyl-sn-glycero-3-phosphocholine
- Molecular formula
- C20H40NO8P
- Molecular weight
- 453.51
Names & synonyms
1,2-dihexanoyl-sn-glycero-3-phosphocholinePC(6:0/6:0)CHEBI:138194RefChem:1052260PC(12:0)34506-67-7Dihexanoyllecithin(R)-2,3-Bis(hexanoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate(2-{[(2R)-2,3-bis(hexanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium[(2R)-2,3-di(hexanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphatePC 12:0starbld0018461
Show more names
DHPC06:0 PC06:0 PC (DHPC)Dicaproyl-L-α-lecithinL-α-Dihexanoyllecithin1,2-Dihexanoyl-sn-glycero-3-PCdihexanoyl-l-a-phosphatidylcholineL-A-PHOSPHATIDYLCHOLINE, DICAPROYL
L-|A-DihexanoyllecithinDicaproyl-L-|A-lecithinL-alpha-DihexanoyllecithinL-1,2-DihexanoyllecithinDicaproyl-L-alpha-lecithinSCHEMBL4176491,2-dihexanoyl-sn-glycero-3-phosphocholine (DHPC)C20H40NO8P
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 111 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 20
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 527
Experimental & physicochemical properties
LipidsLipids -> Glycerophospholipids [GP] -> Glycerophosphocholines [GP01] -> Diacylglycerophosphocholines [GP0101]
Physicochemical properties
- storage temp.
- 20 °C · −20°C
- solubility
- 20 mg/ml; · DMF: > 20 mg/ml; DMSO: > 7 mg/ml; Ethanol: > 30 mg/ml; PBS (pH 7.2): > 250 μg/ml
- form
- solution
- color
- White to off-white
- InChI
- 1S/C20H41NO8P/c1-6-8-10-12-19(22)26-16-18(29-20(23)13-11-9-7-2)17-28-30(24,25)27-15-14-21(3,4)5/h18H,6-17H2,1-5H3,(H,24,25)
- InChIKey
- KGWWHBYICAIILE-UHFFFAOYSA-N
- SMILES
- [O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OC(CCCCC)=O)COC(CCCCC)=O)=O
- UNSPSC Code
- 51191904 · 51191904
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 6 · GHS06,GHS08
- Signal word
- Danger
- Hazard statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P264, P270, P280, P301+P317, P302+P352, P318, P319, P321, P330, P332+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 1888 6.1/PG 3
- risk_code
- 22-38-40-48/20/22-36/38-20/22-63
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- Xn
- safety_code
- 36/37-26
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Central nervous system, Liver,Kidney
- Hazard statements
- H302-H315-H319-H331-H336-H351-H361d-H372-H412
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 3Carc. 2Eye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 1STOT SE 3
Chemistry & industry
Applications
Description1,2-Dihexanoyl-sn-glycero-3-PC (DHPC-C6) is a synthetic phospholipid containing the short-chain (6:0) caproic acid inserted at the sn-1 and sn-2 positions. It is a substrate for phospholipase C isolated from B. cereus as well as phospholipase A2 isolated from A. halys blomhoffi and N. naja atra snake venom. DHPC is commonly used in the generation of micelles, liposomes, and other types of artificial membranes.
UsesL-α-Dihexanoyllecithin is used in the targeted delivery of adamantylated peptidoglycan immunomodulators in lipid nanocarriers.
Additional notes
DefinitionChEBI: 1,2-dihexanoyl-sn-glycero-3-phosphocholine is a phosphatidylcholine 12:0 in which both acyl groups are specified as hexanoyl. It has a role as a surfactant. It is functionally related to a hexanoic acid.
Related reactions
0 records
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Compound notes
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