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R7632

Sigma-Aldrich

Retinol

synthetic, ≥95% (HPLC), crystalline

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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
Empirical Formula (Hill Notation):
C20H30O
CAS Number:
Molecular Weight:
286.45
Beilstein:
403040
EC Number:
MDL number:
eCl@ss:
34058018
PubChem Substance ID:
NACRES:
NA.79

biological source

synthetic

Quality Level

Assay

≥95% (HPLC)

form

crystalline

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

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This Item
95144R5754V-011
Retinol synthetic, ≥95% (HPLC), crystalline

Sigma-Aldrich

R7632

Retinol

-
Retinol BioXtra, ≥97.5% (HPLC), ~3100 U/mg

Sigma-Aldrich

95144

Retinol

Premium Grade
9-cis-Retinal vitamin A analog

Sigma-Aldrich

R5754

9-cis-Retinal

-
Retinol solution 100 μg/mL ± 25% (Refer to COA) (Ethanol with 0.1% (w/v) BHT), ampule of 1 mL, reference material, Cerilliant®

Supelco

V-011

Retinol solution

-
assay

≥95% (HPLC)

assay

≥97.5% (HPLC)

assay

≥95% (HPLC)

assay

-

form

crystalline

form

powder

form

powder

form

liquid

technique(s)

HPLC: suitable

technique(s)

-

technique(s)

HPLC: suitable

technique(s)

-

color

yellow to very dark yellow, to Very Dark Orange

color

faint yellow to very dark yellow

color

yellow to yellow-orange

color

-

mp

61-63 °C (lit.)

mp

56-61 °C, 61-63 °C (lit.)

mp

56-58 °C (lit.)

mp

-

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.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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T1503
Product Number
-
25G
Pack Size/Quantity

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705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

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  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

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Retinol acetate European Pharmacopoeia (EP) Reference Standard

R0300000

Retinol acetate

(±)-α-Tocopherol synthetic, ≥96% (HPLC)

Sigma-Aldrich

T3251

(±)-α-Tocopherol

Retinyl palmitate Type IV, ~1,800,000 USP units/g, oil

Sigma-Aldrich

R3375

Retinyl palmitate

9-cis-Retinal vitamin A analog

Sigma-Aldrich

R5754

9-cis-Retinal

Retinyl acetate solid or viscous liquid, BioReagent, synthetic, suitable for cell culture

Sigma-Aldrich

R7882

Retinyl acetate

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)
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)
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)
Valproate ameliorates nitroglycerin-induced migraine in trigeminal nucleus caudalis in rats through inhibition of NF-?B.
Li Y et al.
The Journal of Headache and Pain, 17, 49-49 (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)

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.

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