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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 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.
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.

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
BCCP3021
BCCP5774
BCCP6444
BCCP6443
BCCM6917

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Insulin regulates retinol dehydrogenase expression and all-trans-retinoic acid biosynthesis through FoxO1.
Obrochta KM et al.
The Journal of Biological Chemistry, 290, 7259-7259 (2015)
Retinol Promotes In Vitro Growth of Proximal Colon Organoids through a Retinoic Acid-Independent Mechanism.
Matsumoto T et al.
PLoS ONE, 11, e0162049-e0162049 (2016)
A newly synthesized photostable retinol derivative (retinyl N-formyl aspartamate) for photodamaged skin: profilometric evaluation of 24-week study
Lee MS, et al.
Journal of the American Academy of Dermatology, 55(2), 220-224 (2006)
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