11-Cis-Retinal

HCID 5280490

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Basic information

CAS: 564-87-4
Standard SMILES: CC1=C(/C=C/C(C)=C/C=C\C(C)=C\C=O)C(C)(C)CCC1
InChIKey: NCYCYZXNIZJOKI-IOUUIBBYSA-N
Molecular formula: C20H28O
Average molar mass: 284.4 g/mol
Monoisotopic mass: 284.21401552

Overview

11-cis-retinal is a retinal having 2E,4Z,6E,8E-double bond geometry. It has a role as a chromophore, a mouse metabolite and a human metabolite.

Names & identifiers

Preferred name: 11-Cis-Retinal
IUPAC: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
English name: 11-cis Retinal
Molecular formula: C20H28O
Molecular weight: 284.44

Names & synonyms

11-cis-Retinal564-87-411-cis-Retinaldehyde(11Z)-RetinalNeoretinene b11-cis-Vitamin A aldehydeRetinal, (11Z)-11-cis-Retinene91058V6HCH(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenalCHEBI:16066DTXSID80415057

Show more names

Retinal, 11-cis-11cis Retinal,11 cis Retinal11-cis-Retinal (>65%), in Benzene (0.5mg/mL)(2E,4Z,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenal(2E,4Z,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenal

(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenalRefChem:907974DTXCID4036590811-cis Retinal11-cis-Retinal [MI]UNII-91058V6HCHRHODOPSIN11-cis-Retinal (>65%)

Database identifiers

CAS: 564-87-4
PubChem CID: 5280490
DTXSID: DTXSID80415057
ChEMBL: CHEMBL1255087
ChEBI: CHEBI:16066
UNII: 91058V6HCH
Nikkaji: J1.631.404H、J1.631.405F、J439.005I

Properties

Computed structural properties

XLogP: 6.2
Topological polar surface area: 17.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 5
Heavy atoms: 21
Formal charge: 0
Complexity: 522

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]

Melting Point63.5 - 64.4 °C

Physical DescriptionSolid

Physicochemical properties

Boiling point: 421.4 · 421.4±14.0 °C(Predicted)
Density: 1.07 g/cm3 · 1.07 g/cm3
storage temp.: -86 °C · Amber Vial, -86°C Freezer, Under Inert Atmosphere
solubility: Chloroform (Slightly), Ethanol (Slightly), Ethyl Acetate (Slightly)
form: Sticky Yellow Solution
color: Yellow to Dark
Stability: Light Sensitive, Temperature Sensitive
FDA UNII: 91058 V6HCH · 91058V6HCH
Symbol(GHS): 7 · GHS07,GHS08
Signal word: Warning
Hazard statements: 302 · H302-H315-H361
Precautionary statements: 201 · P201-P202-P264-P270-P280-P301+P312-P330-P302+P352-P308+P313-P321-P362+P364-P332+P313-P405-P501

Safety & regulation

Safety data

Signal word: Warning
Symbol(GHS): GHS07,GHS08
Hazard statements: H302-H315-H361
Precautionary statements: P201-P202-P264-P270-P280-P301+P312-P330-P302+P352-P308+P313-P321-P362+P364-P332+P313-P405-P501