9-cis-Retinal

HCID 6436082CAS 514-85-2

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Grundinformationen

Standard-SMILES: CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C=O)C(C)(C)CCC1
InChIKey: NCYCYZXNIZJOKI-MKOSUFFBSA-N
Summenformel: C20H28O
Durchschnittliche Molmasse: 284,4 g/mol
Monoisotopische Masse: 284,21401552

Überblick

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.

Namen und Bezeichner

Bevorzugter 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
Lokaler Name: 9-cis-Retinal
Englischer Name: 9-CIS-RETINAL
Summenformel: C20H28O
Molmasse: 284.44

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

CAS: 514-85-2
PubChem CID: 6436082
DTXSID: DTXSID00891233
ChEMBL: CHEMBL257381
ChEBI: CHEBI:78273
EC Number: 208-188-8
Nikkaji: J1.631.398J、J1.631.399H、J121.827A

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 6,2
Polarare Oberfläche (TPSA): 17,1 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 1
Frei drehbare Bindungen: 5
Schwere Atome: 21
Formalladung: 0
Komplexität: 522

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Vitamins and Derivatives

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

Physical Description · 2 Einträge

Solid; [Sigma-Aldrich MSDS]

Solid

Collision Cross Section170.1 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physikochemische Eigenschaften

Schmelzpunkt: 56 · 56-58 °C(lit.)
Siedepunkt: 366.92 °C · 366.92°C (rough estimate)
Dichte: 1.0083 · 1.0083 (rough estimate)
Brechungsindex: 1.45 · 1.4500 (estimate)
storage temp.: 20 °C · −20°C
Löslichkeit: Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand: Solid
Farbe: Yellow to Orange
Stabilität: Light Sensitive, Temperature 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+
InChIKey: NCYCYZXNIZJOKI-MKOSUFFBSA-N
SMILES: CC(=C\C=O)/C=C/C=C(C)\C=C\C1=C(C)CCCC1(C)C
EPA chemische Informationen: 9 · Retinal, 9-cis- (514-85-2)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazards SummaryA skin irritant; Harmful by ingestion, inhalation, and skin absorption; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

wgk: 3
tsca: TSCA listed
RTECS-Nr.: VH6406500
risk_code: 20/21/22-38
hazard_code: Xn
safety_code: 22-36/37
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralSkin Irrit. 2

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites9-cis-retinal has known human metabolites that include 4-hydroxy-9-cis-retinals.

Cellular LocationsCytoplasm

Metabolite PathwaysRetinol Metabolism

Verwendung und Herstellung

General Manufacturing InformationRetinal, 9-cis-: INACTIVE

Anwendungen

Verwenden9-cis-Retinal is an isomer of all-trans-Retinal (R240000).

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

magnesium,ethynoxyethane,bromide, Fandachem Retinal, (9-cis,13-cis)-4,4-Diethoxy-2-methylbut-1-ene Retinylacetat 9-cis-Retinoic acid methyl ester (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol 11-cis Retinal 13-cis-Retinal Vitamin-A-alkohol

Anbieter31 Anbieter

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

南京瓦力化工科技有限公司18005141382 · [email protected]

上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A retinal in which the double bond at position 9 has cis configuration, whilst the remaining acyclic double bonds have trans configuration.