| Identification | More | [Name]
ALL-TRANS-RETINAL | [CAS]
116-31-4 | [Synonyms]
ALL-TRANS-RETINAL
ALL-TRANS-VITAMIN-A-ALDEHYDE
RETINAL ALL TRANS
VITAMIN A ALDEHYDE
2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-
2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-
all-E-Retinal
all-trans-retina
All-trans-Retinaldehyde
alpha-Retinene
Axerophthal
E-Retinal
Retinaldehyde
Retinene
Retinene1
trans-Retinal
trans-Vitamin A aldehyde
trans-vitaminaaldehyde
Vitamin A1 aldehyde
vitamina1aldehyde | [EINECS(EC#)]
204-135-8 | [Molecular Formula]
C20H28O | [MDL Number]
MFCD00001550 | [Molecular Weight]
284.44 | [MOL File]
116-31-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Powder | [Melting point ]
61-63°C | [Boiling point ]
366.92°C (rough estimate) | [density ]
1.0083 (rough estimate) | [refractive index ]
1.4500 (estimate) | [storage temp. ]
−20°C
| [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
powder
| [color ]
yellow
| [biological source]
synthetic (organic) | [Water Solubility ]
<70mg/L(25 ºC) | [Usage]
Corotenoid component of the visual pigments | [Stability:]
Hygroscopic, Light Sensitive, Temperature Sensitive | [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 | [SMILES]
C(=O)/C=C(/C=C/C=C(/C=C/C1C(C)(C)CCCC=1C)\C)\C | [Uses]
retinaldehyde is a mild retinoid credited with increasing epidermal thickness without producing erythema. | [CAS DataBase Reference]
116-31-4(CAS DataBase Reference) | [EPA Substance Registry System]
Retinal (116-31-4) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R38:Irritating to the skin. | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [RTECS ]
VH6407000
| [HS Code ]
29122990 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Powder | [Definition]
ChEBI: A retinal in which all four exocyclic double bonds have E- (trans-) geometry. | [Synthesis Reference(s)]
Tetrahedron Letters, 29, p. 419, 1988 DOI: 10.1016/S0040-4039(00)80111-2 | [General Description]
All 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. | [Biological Activity]
all-trans retinal, also known as vitamin a aldehyde or retinaldehyde, is one of the many forms of vitamin a and also the oxidation product of all-trans retinol [1]. all-trans retinal are associated with one of the two isoforms of cellular retinol-binding proteins (crbp-i and crbp-ii) with kd values of 50 and 90 nm, respectively [1].crbp-i and crbp-ii were the first intracellular retinoid-binding proteins. both proteins display a similar binding affinity towards retinal. they play important roles in retinoid biology and regulation of the metabolism of retinol and retinal. crbp-i is used to regulate vitamin a storage and synthesis of retinoic acid. and crbp-ii has a role in the initial processing of retinol from food [1].all-trans retinal is one form of vitamin a. all-trans retinal, the initial substrate of retinoid cycle, is a chemically reactive aldehyde that can form toxic conjugates with proteins and lipids, leading to degeneration of the retina [2]. | [Biochem/physiol Actions]
All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase. Retinoic acid is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR) that act as transcription factors to regulate the growth and differentiation of normal and malignant cells. Retinal isomers are also chromophores that bind to opsins, a family of G-protein-linked transmembrane proteins, to form photosensitive receptors in visual and nonvisual systems. All-trans retinal is a potent photosensitizer. | [Purification Methods]
The aldehyde is separated from retinol by column chromatography on water-deactivated alumina. Elute with 1-2% acetone in hexane, or on TLC plates of silica gel G and using the same eluting solvent. It crystallises from pet ether or n-hexane as yellow-orange crystals, and the UV in hexane has max at 373nm (A1cm 1% 1,548) and 368nm ( 48,000). It is an irritant and is light sensitive. Store it in sealed ampoules under N2. The semicarbazone forms yellow crystals from CHCl3/Et2O or EtOH, m 199-201o(dec). The 9-cis-isomer [514-85-2] and the 13-cis-isomer [472-86-6] [max at 375nm ( 1,250) in EtOH] are also available commercially. [Beilstein 7 III 1742.] | [References]
[1]. noy n. retinoid-binding proteins: mediators of retinoid action. biochem j. 2000 jun 15;348 pt 3:481-95.
[2]. kiser pd, golczak m, maeda a, et al. key enzymes of the retinoid (visual) cycle in vertebrate retina. biochim biophys acta. 2012 jan;1821(1):137-51. |
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