CAS 116-31-4 Retinal (HCID 638015)

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Basic information

CAS: 116-31-4
Standard SMILES: CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=O)C(C)(C)CCC1
InChIKey: NCYCYZXNIZJOKI-OVSJKPMPSA-N
Molecular formula: C20H28O
Average molar mass: 284.4 g/mol
Monoisotopic mass: 284.21401552

Overview

All-trans-retinal is a retinal in which all four exocyclic double bonds have E- (trans-) geometry. It has a role as a gap junctional intercellular communication inhibitor, a mouse metabolite and a human metabolite. It is a vitamin A and a retinal.

Names & identifiers

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

Names & synonyms

all-trans-Retinalretinaltrans-Retinal116-31-4retinaldehydevitamin A aldehyderetineneaxerophthalall-E-RetinalE-RetinalRetinene 1all-trans-Retinaldehyde

Show more names

Nanoactive RALRetinylaldehydeRetinene1

Vitamin A1 aldehydeall-trans-Vitamin A aldehydeall-trans-RetineneRetinyl aldehydeRetinal, all-trans(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenalDTXSID5025998

Database identifiers

CAS: 116-31-4、472-86-6
PubChem CID: 638015
DTXSID: DTXSID5025998
ChEMBL: CHEMBL81379
ChEBI: CHEBI:17898
UNII: RR725D715M
EC Number: 204-135-8
Nikkaji: J1.003.612G、J1.826.581H、J5.279E、J861.440G

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]

CosmeticsPersonal care product

SpringerMaterials PropertiesAngular frequency

Melting Point63 °C

Physical DescriptionSolid

Collision Cross Section · 2 items

170.1 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

165.39 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 61 · 61-63°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)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (28.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P317, P302+P352, P318, P321, P330, P332+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 147 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (28.6%)

Safety data

wgk: 3
tsca: TSCA listed
rtecs: VH6407000
hs_code: 29122990
risk_code: 22-38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 22-36/37
Hazard statements: H302-H315
Precautionary statements: P280

Chemistry & industry

Pharmacology

Metabolism/MetabolitesRetinal has known human metabolites that include Tretinoin.

Tissue LocationsAdrenal Cortex

Cellular LocationsCytoplasm

Metabolite PathwaysRetinol Metabolism

Uses & manufacturing

General Manufacturing InformationRetinal: ACTIVE

Applications · 4 items

UsesCorotenoid component of the visual pigments. All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase.

UsesAll trans-Retinal has been used:in optogenetic experiments in electrophysiological experimentto study the effect of AKR1B10 (aldo-keto reductase (AKR) superfamily member) on the conversion of retinal to retinol in the airway epitheliumin decidual transformation of human endometrial stromal cells

Usesretinaldehyde is a mild retinoid credited with increasing epidermal thickness without producing erythema.

General DescriptionAll trans-Retinal is one of the major derivatives of vitamin A group. A variety of food serves as a source of vitamin A. It is predominant in liver and among the brightly colored vegetables.