ChemicalBook > CAS DataBase List > Retinal

Retinal

Product Name
Retinal
CAS No.
116-31-4
Chemical Name
Retinal
Synonyms
Retinaldehyde;Retinene;VITAMIN A ALDEHYDE;Retinylaldehyde;Retinal;Retinene1;E-Retinal;Axerophthal;all-E-Retinal;trans-Retinal
CBNumber
CB6703879
Molecular Formula
C20H28O
Formula Weight
284.44
MOL File
116-31-4.mol
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Retinal Property

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
CAS DataBase Reference
116-31-4(CAS DataBase Reference)
EPA Substance Registry System
Retinal (116-31-4)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-38
Safety Statements 
22-36/37
WGK Germany 
3
RTECS 
VH6407000
HS Code 
29122990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
R2500
Product name
all trans-Retinal
Purity
powder, ≥98%
Packaging
25mg
Price
$68.4
Updated
2024/03/01
Sigma-Aldrich
Product number
R2500
Product name
all trans-Retinal
Purity
powder, ≥98%
Packaging
1g
Price
$381
Updated
2024/03/01
Cayman Chemical
Product number
18449
Product name
all-trans Retinal
Purity
≥98%
Packaging
100mg
Price
$44
Updated
2024/03/01
Cayman Chemical
Product number
18449
Product name
all-trans Retinal
Purity
≥98%
Packaging
1g
Price
$235
Updated
2024/03/01
Sigma-Aldrich
Product number
R2500
Product name
all trans-Retinal
Purity
powder, ≥98%
Packaging
100mg
Price
$93.5
Updated
2024/03/01
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Retinal Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Vitamin A EC 1.1.1.1

Preparation Products

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View Lastest Price from Retinal manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
All-trans-retinal 116-31-4
Price
US $35.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/Week
Release date
2024-05-07
WUHAN FORTUNA CHEMICAL CO., LTD
Product
all trans-Retinal 116-31-4
Price
US $0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
500kg/month
Release date
2021-07-28
Sinoway Industrial co., ltd.
Product
alltransretinal 116-31-4
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98% up by hplc
Supply Ability
20 tons
Release date
2024-06-26

116-31-4, RetinalRelated Search:

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

  • 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
  • (2E,4E,6E,8E)-3,7-diMethyl-9-(2,6,6-triMethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
  • Retinylaldehyde
  • all-trans-Retinal,99%
  • all trans-Retinal,VitaminA aldehyde
  • Nanoactive RAL
  • BioActive Retinal
  • Nanoactive RAL,BioaActive retinaldehyde
  • Retinaldehyde ( Retinal, vitamin A aldehyde, ALL-TRANS-RETINAL)
  • Soluble Retinal
  • Soluble Retinaldehyde
  • 2,4,6,8-Nonatetraenal
  • vitamina1aldehyde
  • Vitaminaldehyde
  • ALL-TRANS-RETINAL
  • ALL-TRANS-VITAMIN-A-ALDEHYDE
  • RETINAL ALL TRANS
  • Vitamin A Aldehyde, Retinene
  • 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenal
  • (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal
  • VITAMIN A ALDEHYDE
  • Liposomal Retinylaldehyde, All-trans-retinal
  • Vitamin A Impurity 8（all-trans-Retinal）
  • ALL-TRANS-RETINAL USP/EP/BP
  • Retinaldehyde RAL
  • Retinaldehyde or Retinal CAS 116-31-4 All-Trans-Retinal
  • Vitamin A aldehyde (19,19,19,20,20,20-D6)
  • All-trans-retinal 13C4
  • Sodium N-cyclohexylsulfamate 139-05-9
  • Retinal
  • Retinal,E-Retinal
  • Retinal aldehyde
  • 116-31-4
  • BioChemical
  • Antitumor Agents
  • Cancer Research
  • Gene Regulation
  • Vitamins
  • Aldehydes
  • Antitumor Agents
  • Building Blocks
  • C13-C60
  • Cancer Research
  • Carbonyl Compounds