13-cis-Retinal
Basic information
- CAS
472-86-6- Standard SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C\C=O)C(C)(C)CCC1- InChIKey
NCYCYZXNIZJOKI-HWCYFHEPSA-N- Molecular formula
- C20H28O
- Average molar mass
- 284.4 g/mol
- Monoisotopic mass
- 284.21401551
Overview
13-cis-retinal is a retinal in which the double bond alpha- to the aldehyde group has cis configuration, whilst the remaining acyclic double bonds have trans configuration. It has a role as a human metabolite.
Names & identifiers
- Preferred name
- 13-cis-Retinal
- IUPAC
- (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
- English name
- 13-CIS-RETINAL
- Molecular formula
- C20H28O
- Molecular weight
- 284.44
Names & synonyms
13-cis-Retinal472-86-613-cis-RetinaldehydeNeoretinene a13Z-RetinalNeovitamin A aldehydeRetinal, 13-cis-(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenalDTXSID0025997(13cis)-retinalRetinal, (13Z)-IBP64540CD
Show more names
13-cis-retina(13Z)-Retinal13-DIS-RETINALcis-13-retinal2-CIS-VITAMIN A ALDEHYDE
(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenalDTXCID805997CHEBI:45487NSC-122756(2Z,4E,6E,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-1-CYCLOHEXENYL)NONA-2,4,6,8-TETRAENALDTXSID00859212RefChem:78413DTXCID80809679
Database identifiers
- CAS
472-86-6- PubChem CID
- 6436079
- DTXSID
DTXSID0025997- ChEMBL
CHEMBL1579130- ChEBI
CHEBI:45487- UNII
- IBP64540CD
Properties
Computed structural properties
- XLogP
- 6.2
- Topological polar surface area
- 17.1 Ų
- 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]
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 65 · 65-69°C
- Boiling point
- 366.92 °C · 366.92°C (rough estimate)
- Density
- 1.0083 · 1.0083 (rough estimate)
- refractive index
- 1.45 · 1.4500 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Yellow to Dark Yellow
- biological source
- synthetic (organic)
- Stability
- Light Sensitive
- InChI
- 1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13-
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]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P332+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 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
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- risk_code
- 20/21/22-38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H312-H315-H332
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralSkin Irrit. 2
- Precautionary statements
- P280
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
General Manufacturing InformationRetinal, 13-cis-: ACTIVE
Applications
UsesAn isomer of all-trans-Retinal (R240000).
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A retinal in which the double bond alpha- to the aldehyde group has cis configuration, whilst the remaining acyclic double bonds have trans configuration.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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