Retinal Chemical Properties

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

Water Solubility 

<70mg/L(25 ºC)

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

CAS DataBase Reference

116-31-4(CAS DataBase Reference)

EPA Substance Registry System

Retinal (116-31-4)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-38

Safety Statements 

22-36/37

WGK Germany 

3

RTECS 

VH6407000

HS Code 

29122990

MSDS

• Language:English Provider:SigmaAldrich

Retinal Usage And Synthesis

Chemical Properties

Yellow Powder

Uses

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

Uses

All trans-Retinal has been used:

• in optogenetic experiments
• in electrophysiological experiment
• to study the effect of AKR1B10 (aldo-keto reductase (AKR) superfamily member) on the conversion of retinal to retinol in the airway epithelium
• in decidual transformation of human endometrial stromal cells

Uses

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

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.

Retinal(116-31-4)Related Product Information

• COENZYME
• CHLOROPHYLL
• Collagen
• Ascorbic Acid
• Vitamin A
• Folic acid
• β-Carotene
• Vitamin E
• Nicotinic acid
• Vitamin A palmitate
• 3-Cyclohexene-1,2-dimethanol, 3,6-dimethyl-5-[2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-butadienyl]-6-[4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5-hexatrienyl]-, cis-2,cis-5- (8CI)
• Kitol Diacetate(Mixture of Diastereomers)
• 9-cis-Retinyl Palmitate
• (3E,5E,7E)-9-[(3E)-2,4,4-Trimethyl-1-cyclohexen-3-ylidene]-3,7-dimethylnona-3,5,7-trien-1-ol
• anhydrovitamin A
• (Z)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one
• 13-Cis Vitamin A Palmitate
• 4-(2,2-dimethyl-6-methylenecyclohexyl)-3-buten-2-one