(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

• ChemBase ID: 125064
• Molecular Formular: C20H28O
• Molecular Mass: 284.43572
• Monoisotopic Mass: 284.21401552
• SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=O)/C)/C
• Canonical SMILES: O=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
• InChI: 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-OVSJKPMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
• IUPAC Traditional name: retinaldehyde
• Synonyms: (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal; all -trans-Vitamin A Aldehyde; Retinene; all trans-Retinal; retinaldehyde; vitamin A aldehyde; RAL; Retinal; All-trans-retinal; ALL-TRANS-RETINAL; 维生素 A 醛; 全反式视黄醛; 视黄醛

Database IDs

• CAS Number: 116-31-4
• EC Number: 204-135-8
• MDL Number: MFCD00001550
• PubChem SID: 24899355; 162219414
• PubChem CID: 638015; 1070
• Unique Ingredient Identifier: RR725D715M
• Wikipedia Title: Retinal

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.8557515
• LogD (pH = 7.4): 4.8557515
• Log P: 4.8557515
• Molar Refractivity: 96.8654 cm^3
• Polarizability: 35.792797 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Clear Yellow Solution at 5mg/ml Acetonitrile.; nearly insoluble in water; soluble in fat
• Apperance: orange crystals from petr ether; yellow powder; Yellow to Orange Solid
• Melting Point: 58-63°C; 61-64 °C

Safety Information

• Storage Condition: Amber Vial, -18°C Freezer, Under Inert Atmosphere
• RTECS: VH6407000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-38
• Safety Statements: 22-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Shipped in: dry ice

DETAILS

Sigma Aldrich - R2500

Biochem/physiol Actions
全反式视黄醛在体内可通过视黄醛脱氢酶作用转化为视黄酸。视黄酸是视黄酸受体 (RAR) 和类视色素 X 受体 (RXR) 的配体，这两种受体作为转录因子调控正常和恶性细胞的生长和分化。在可视和非可视系统中，视黄醛异构体也是发色团，可与 G-蛋白偶联跨膜蛋白家族的视蛋白结合，形成光敏受体。全反式视黄醛是一种强效的光敏剂。
包装
密封安瓿瓶。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R2500.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - R240000

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

REFERENCES

• Ball, et al.: Biochem. J., 42, 516 (1948)
• O’Brien, D.F., et al.: Science, 218, 961 (1948)