79-80-1

Basic information

• Product Name: dehydroretinol
• Synonyms: dehydroretinol;(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraen-1-ol;3,4-Dehydroretinol;3-Dehydroretinol;all-trans- 3-Dehydroretinol;all-trans-3,4-Didehydroretinol;Vitamin A2;Retinol, 3,4-didehydro-
• CAS NO: 79-80-1
• Molecular Formula: C₂₀H₂₈O
• Molecular Weight: 284.44
• EINECS: 201-226-4
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids;Pharmaceuticals, Intermediates & Fine Chemicals, Retinoids
• Mol File: 79-80-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 63-650C
• Boiling Point: 425.6°C at 760 mmHg
• Flash Point: 151.4°C
• Appearance: /
• Density: 0.969g/cm³
• Vapor Pressure: 5.01E-09mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: Hygroscopic, -86°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: dehydroretinol(CAS DataBase Reference)
• NIST Chemistry Reference: dehydroretinol(79-80-1)
• EPA Substance Registry System: dehydroretinol(79-80-1)

Safety Data

• Hazardous Substances Data: 79-80-1(Hazardous Substances Data)

Usage

Chemical Properties

Light-Yellow Crystalline Solid

Uses

Different sources of media describe the Uses of 79-80-1 differently. You can refer to the following data:
1. Naturally occurring retinoid originally discovered in livers of freshwater fish. Constitutes 20-25% of total retinoid content in human epidermis; levels are markedly elevated in patients with hyperproliferative dermatoses such as psoriasis
2. Naturally occurring retinoid originally discovered in livers of freshwater fish. Constitutes 20-25% of total retinoid content in human epidermis; levels are markedly elevated in patients with hyperproliferative dermatoses such as psoriasis.

Definition

ChEBI: A retinoid derived from 3,4-desaturation of the beta-ionone ring of all-trans-retinol.

InChI:InChI=1/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6-13,21H,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

Upstream product

• 472-87-7 3,4-didehydroretinal 
• 6153-05-5 (Z)-3-methylpent-2-en-4-ynol 
• 100862-93-9 (E)-2-Methyl-4-(2,6,6-trimethyl-cyclohexa-1,3-dienyl)-but-2-enal 
• 68-26-8 RETINOL 
• 24041-43-8 methyl (7E,9E,11E,13E)-9,13-dimethyl-7-(1,1,5-trimethyl-3,5-cyclohexadien-6-yl)-7,9,11,13-nonatetraen-15-oate 
• 60-29-7 diethyl ether 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 26918-26-3 ethyl 3,4-didehydroretinoate 
• 817203-14-8 1-[(trifluoromethanesulfonyl)oxy]-2,6,6-trimethylcyclohexa-1,3-diene 
• 14398-42-6 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid 
• 14538-58-0 3-methyl-5t-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2t,4-dienoic acid methyl ester 
• 4159-20-0 3,4-didehydroretinoic acid 
• 25528-85-2 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohexa-1,3-dienyl)penta-2,4-dien-1-ol 

Downstream Products

• 472-87-7 3,4-didehydroretinal 
• 124130-50-3 9-(4-Phenylazo-benzoyloxy)-3.7-dimethyl-1t-[2.2.6-trimethyl-cyclohexadien-(4.6)-(yl)-nonatetraen-(1.3t.5t.7t) 
• 95632-86-3 dehydroretinyl palmitate 
• 7640-75-7 ethyl-[4-(3,7-dimethyl-nona-2,4,6,8-tetraenylidene)-3,5,5-trimethyl-cyclohex-2-enyl]-ether 
• 6890-93-3 3-hydroxyretinol 

Relevant articles and documents

-

-

Substrate specificity and subcellular localization of the aldehyde-Alcohol redox-Coupling reaction in carp cones

Our previous study suggested the presence of a novel conespecific redox reaction that generates 11-cis-retinal from 11-cisretinol in the carp retina. This reaction is unique in that 1) both 11-cis-retinol and all-trans-retinal were required to produce 11-cis-retinal; 2) together with 11-cis-retinal, all-trans-retinol was produced at a 1:1 ratio; and 3) the addition of enzyme cofactors such as NADP(H) was not necessary. This reaction is probably part of the reactions in a cone-specific retinoid cycle required for cone visual pigment regeneration with the use of 11-cis-retinol supplied from Mueller cells. In this study, using purified carp cone membrane preparations, we first confirmed that the reaction is a redox-coupling reaction between retinals and retinols. We further examined the substrate specificity, reaction mechanism, and subcellular localization of this reaction. Oxidation was specific for 11-cis-retinol and 9-cis-retinol. In contrast, reduction showed low specificity: many aldehydes, including all-trans-, 9-cis-, 11-cis-, and 13-cis-retinals and even benzaldehyde, supported the reaction. On the basis of kinetic studies of this reaction (aldehyde-alcohol redox-coupling reaction), we found that formation of a ternary complex of a retinol, an aldehyde, and a postulated enzyme seemed to be necessary, which suggested the presence of both the retinol- and aldehydebinding sites in this enzyme. A subcellular fractionation study showed that the activity is present almost exclusively in the cone inner segment. These results suggest the presence of an effective production mechanism of 11-cis-retinal in the cone inner segment to regenerate visual pigment.

Iron(III)Porphinate/H2O2-Mediated Conversion of All-(E)-Retinol

The reaction of hydrogen peroxide with all-(E)-retinol (1) catalyzed by (meso-tetraphenylporphinato)iron(III) led to the formation of 4-hydroxyretinol (2), 4-oxoretinol (3), 5,8-epoxyretinol (4), 5,6-epoxyretinol (5), 3-dehydroretinol (6), all-(E)- and 12-(Z)-retroretinol (7/7a) as well as all-(E)- and 12-(Z)-anhydroretinol (8/8a) as major non-volatile products.The conversion products were characterized by comparison of their chromatographic (HPLC) and spectroscopic data (UV; MS; 1H and 13C NMR) with those of synthesized reference compounds.The observed product formation supports the hypothesis of a C4 centered radical as the key intermediate of all-(E)-retinol conversion. - Keywords: 5,6- and 5,8-Epoxyretinol, 4-Hydroxyretinol, 4-Oxoretinol, Retinol Conversion