Basic information
- CAS
514-85-2- Standard SMILES
CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=O)C(C)(C)CCC1- InChIKey
NCYCYZXNIZJOKI-MKOSUFFBSA-N- Molecular formula
- C20H28O
- Average molar mass
- 284.4 g/mol
- Monoisotopic mass
- 284.21401552
Overview
9-cis-retinal is a retinal in which the double bond at position 9 has cis configuration, whilst the remaining acyclic double bonds have trans configuration.
Names & identifiers
- Preferred name
- 9-Cis-Retinal
- IUPAC
- (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
- English name
- 9-CIS-RETINAL
- Molecular formula
- C20H28O
- Molecular weight
- 284.44
Names & synonyms
9-cis-Retinal514-85-29-cis-RetinaldehydeIsoretinene A9-cis-Vitamin A aldehyde9-C-RetinalRetinal, 9-cis-9-cis-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenalCHEBI:78273DTXSID00891233(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenal
Show more names
C031390isoretinenea(9Z)-Retinalcis-9-retinal
RefChem:5493143,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenalDTXCID801030416208-188-8(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal(9cis)-retinalIso Rhodopsin9-cis-7,11,13-trans-retinal
Database identifiers
- CAS
514-85-2- PubChem CID
- 6436082
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
Chemical ClassesBiological Agents -> Vitamins and Derivatives
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
Physical Description
Solid; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section170.1 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 56 · 56-58 °C(lit.)
- 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), Methanol (Slightly)
- form
- Solid
Safety & regulation
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
Hazards SummaryA skin irritant; Harmful by ingestion, inhalation, and skin absorption; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- VH6406500
- risk_code
- 20/21/22-38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332-H315
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralSkin Irrit. 2
- Precautionary statements
- P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
Chemistry & industry
Pharmacology
Metabolism/Metabolites9-cis-retinal has known human metabolites that include 4-hydroxy-9-cis-retinals.
Cellular LocationsCytoplasm
Metabolite PathwaysRetinol Metabolism
Uses & manufacturing
General Manufacturing InformationRetinal, 9-cis-: INACTIVE
Applications
Uses9-cis-Retinal is an isomer of all-trans-Retinal (R240000).
Upstream & downstream products
Upstream raw materials
Related reactions
3 records
Compound notes
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