Molecule
ID:125064
General Information
Molecular Formula
C₂₀H₂₈O
Molecular Mass
284.43572
Exact Mass
284.21401552
Charge
0
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
Canonic Smiles
O=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
Isomeric Smiles
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=O)/C)/C
Calculated Properties
JChem
LogD (pH = 7.4)
4.86
LogD (pH = 5.5)
4.86
Log P
4.86
Rotatable Bonds
5
H Donor
0
H Acceptors
1
Lipinski's Rule of Five
true
Acid pKa
-4.06
Polar Surface Area
17.07
Polarizability
35.75
Molar Refractivity
96.87
LOG S
-6.99
Data Source
Commercial Catalog
Names and Identifiers
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
维生素 A 醛vitamin A aldehydeall trans-Retinal视黄醛retinaldehydeRetinalRALAll-trans-retinal全反式视黄醛all -trans-Vitamin A AldehydeRetinene(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenalALL-TRANS-RETINALall-trans-retinalall-trans-retinalvitamin A1 aldehydetrans-vitamin A aldehydeall-trans-retineneall-E-retinalretineneretinene 1trans-retinalall-trans-vitamin A aldehydeE-retinalretinaldehydeaxerophthalvitamin A aldehydeall-trans-retinaldehyderetinyl aldehyderetinal
Registration numbers
CAS Number
MDL Number
EC Number
Wikipedia Title
Unique Ingredient Identifier
PubMed Citation Links
BRENDA Database
Protein Data Bank
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
UniProt Database
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
SureChEMBL Database
LIPID MAPS Instance
CompTox Database
Reaxys Registry
MetaCyc Database
KEGG ID
CHEMBL
Rhea Database
Patent number
Reactom Database
IntEnz Database
PDBeChem Database
EnzymePortal Database
VirtualMetabolicHuman Database
Chemspider ID
FooDB Database
Carotenoids Database
NMRShiftDB Database
GeneOntology Database
SwissLipids Database Link
HMDB Database
Properties
Physical Property
Melting Point
61-64 °C
58-63°C
Solubility
soluble in fat
nearly insoluble in water
Clear Yellow Solution at 5mg/ml Acetonitrile.
Apperance
orange crystals from petr ether
yellow powder
Yellow to Orange Solid
Safety Information
GHS Signal Word
Warning
Storage Temperature
-20°C
RTECS
VH6407000
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
German water hazard class
3
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
European Hazard Symbols
Harmful (Xn)MSDS Link
Storage Condition
Amber Vial, -18°C Freezer, Under Inert Atmosphere
Product Information
Related Proteins
Molecular Spectra
No Data Available
Click here to submit data
Molecule Details
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.
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.
Corotenoid component of the visual pigments. All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase.
A retinal in which all four exocyclic double bonds have E- (trans-) geometry.
References
PubChem Literature
From Data Sources
• Ball, et al.: Biochem. J., 42, 516 (1948)
• O’Brien, D.F., et al.: Science, 218, 961 (1948)
Bioactivity
PubChem BioAssay