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

Description

Dehydroretinol is a naturally occurring retinoid originally discovered in the livers of freshwater fish. It is a derivative of all-trans-retinol, formed through the 3,4-desaturation of the beta-ionone ring. Dehydroretinol constitutes 20-25% of the total retinoid content in human epidermis and is found in higher levels in patients with hyperproliferative dermatoses such as psoriasis. It is a light-yellow crystalline solid.

Uses

Used in Pharmaceutical Industry:
Dehydroretinol is used as a therapeutic agent for treating hyperproliferative skin conditions such as psoriasis. Its presence in higher levels in affected patients suggests a potential role in regulating skin cell proliferation and differentiation.
Used in Cosmetic Industry:
Dehydroretinol is used as an active ingredient in anti-aging and skin care products. Its ability to modulate retinoid signaling pathways may contribute to improved skin texture, reduced appearance of fine lines and wrinkles, and enhanced skin firmness.
Used in Research:
Dehydroretinol serves as a valuable compound in scientific research, particularly in the study of retinoid metabolism, signaling pathways, and their role in various physiological processes. It can be used to investigate the mechanisms underlying its effects on skin cell proliferation and differentiation, as well as its potential therapeutic applications in other conditions.

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

• 68-26-8 RETINOL 
• 22737-96-8 11-cis-retinol 
• 472-87-7 3,4-didehydroretinal 
• 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 
• 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 
• 4159-20-0 3,4-didehydroretinoic acid 
• 14538-58-0 3-methyl-5t-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2t,4-dienoic acid methyl ester 
• 14398-42-6 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid 
• 6901-91-3 9-trans-Dehydro-β-jonyliden-essigsaeure 
• 25528-87-4 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1,3-cyclohexadienyl)-2,4-pentadienal 
• 25528-85-2 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohexa-1,3-dienyl)penta-2,4-dien-1-ol 
• 817203-14-8 1-[(trifluoromethanesulfonyl)oxy]-2,6,6-trimethylcyclohexa-1,3-diene 
• 26918-26-3 ethyl 3,4-didehydroretinoate 

Downstream Products

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

Relevant articles and documents

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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