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R7632

Retinol

synthetic, ≥95% (HPLC), (Powder or Powder with Lumps)

Synonym(s):

Axerophthol, Vitamin A, Vitamin A alcohol, Vitamin A1, all-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol

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About This Item

Empirical Formula (Hill Notation):
C20H30O
CAS Number:
68-26-8
Molecular Weight:
286.45
NACRES:
NA.79
PubChem Substance ID:
24899395
eCl@ss:
34058018
UNSPSC Code:
12352205
EC Number:
200-683-7
MDL number:
MFCD00001552
Beilstein/REAXYS Number:
403040
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biological source

synthetic

Quality Level

200

assay

≥95% (HPLC)

form

(Powder or Powder with Lumps)

specific activity

~2700 U/mg

technique(s)

HPLC: suitable

color

yellow to very dark yellow, to Very Dark Orange

mp

61-63 °C (lit.)

shipped in

dry ice

storage temp.

−20°C

SMILES string

CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/CO)=C(C)CCC1

InChI

1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChI key

FPIPGXGPPPQFEQ-OVSJKPMPSA-N

General description

Retinol or vitamin A alcohol is the main circulating form of vitamin A. It is not biologically active. Retinol or all-trans-retinol is a 20-carbon molecule with cyclohexenyl ring, a side chain with four double bonds (in trans configuration), and an alcohol end group.

Application

Retinol has been used:
  • for the synthesis of all-trans-retinoic acid in HepG2 cells
  • to study the effect of retinol on the growth of murine normal colonic cells cultured as organoids
  • as a standard for determination of vitamin A in cells
  • as a component of chemically defined medium for testis organ culture and spermatogenesis in vitro.

Biochem/physiol Actions

Retinol works as a precursor of active retinoids. It is converted to retinaldehyde and subsequently to retinoic acid. All-trans and 9-cis-retinoic acid are the ligands for nuclear receptors, retinoic acid receptors (RARs) and retinoid X receptors (RXRs). These receptors are transcriptional regulators of various genes.
Retinol and its derivatives exhibit anti-aging properties. In addition, it also acts as an anti-wrinkle agent. However, due to its photoinstability and skin irritation potency, it is not widely used in cosmetic formulations. Retinol is used in the treatment of dermatoses including photoaging. Its deficiency is associated with the development of xerosis and follicular hyperkeratosis.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.
Light protecting glass vial.

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pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Repr. 1B - Skin Sens. 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF5585
BCCG6660
BCCF0203
BCCD3519
BCCC4725

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Protocols

HPLC Analysis of Vitamins, Fat Soluble (A and E), on SUPELCOSIL™ LC-18

Separation of δ-Tocopherol, analytical standard; Retinyl acetate; (+)-γ-Tocopherol; α-Tocopherol, ≥95.5%; Retinol; Vitamin A (acetate), meets USP testing specifications.

In vitro mouse spermatogenesis with an organ culture method in chemically defined medium.
Sanjo H, et al.
PLoS ONE, 13 (2018)
Understanding the physiological role of retinol-binding protein in vitamin A metabolism using transgenic and knockout mouse models.
Quadro L et al.
Molecular Aspects of Medicine, 24, 421-421 (2003)
Yuanchao Li et al.
The journal of headache and pain, 17, 49-49 (2016-05-07)
As a complex nervous system disease, migraine causes severe healthy and social issues worldwide. Valproate (VPA) is a widely used treatment agent against seizures and bipolar disorder, and its function to alleviate damage due to migraine has also been verified
View All Related Papers

Global Trade Item Number

SKUGTIN
R7632-100MG04061835548323
R7632-1G04061835548330
R7632-250MG04061835548347
R7632-25MG04061835548354
R7632-500MG04061835513994