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44707

Sigma-Aldrich

Acitretin

≥98.0% (HPLC)

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Synonym(s):
9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Empirical Formula (Hill Notation):
C21H26O3
CAS Number:
Molecular Weight:
326.43
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥98.0% (HPLC)

form

powder

SMILES string

COc1cc(C)c(\C=C\C(C)=C\C=C\C(C)=C\C(O)=O)c(C)c1C

InChI

1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+

InChI key

IHUNBGSDBOWDMA-AQFIFDHZSA-N

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1 of 4

This Item
Y0001987PHR15231011007
Acitretin ≥98.0% (HPLC)

44707

Acitretin

Acitretin Pharmaceutical Secondary Standard; Certified Reference Material

PHR1523

Acitretin

Acitretin United States Pharmacopeia (USP) Reference Standard

1011007

Acitretin

form

powder

form

-

form

-

form

-

Quality Level

100

Quality Level

-

Quality Level

300

Quality Level

-

Gene Information

human ... RARA(5914), RARB(5915), RARG(5916), RXRA(6256), RXRB(6257), RXRG(6258)

Gene Information

human ... RARA(5914), RARB(5915), RARG(5916), RXRA(6256), RXRB(6257), RXRG(6258)

Gene Information

human ... RARA(5914), RARB(5915), RARG(5916), RXRA(6256), RXRB(6257), RXRG(6258)

Gene Information

human ... RARA(5914), RARB(5915), RARG(5916), RXRA(6256), RXRB(6257), RXRG(6258)

Application

Acitretin, a retinoid that binds to nuclear receptors and regulates gene expression, is a potent activator of the α-secretase ADAM10 gene expression and apoptosis inducer via the CD95 signalling pathway. Acitretin is a systemic retinoid drug used in the treatment of severe psoriasis.

Biochem/physiol Actions

Synthetic retinoid that is a metabolite of etretinate. Preferentially binds to cellular retinoic acid binding proteins (CRABPs).

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Tretinoin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1187

Tretinoin

Retinyl acetate synthetic, crystalline solid or supercooled liquid

Sigma-Aldrich

R4632

Retinyl acetate

all trans-Retinal powder, ≥98%

Sigma-Aldrich

R2500

all trans-Retinal

Retinoic acid ≥98% (HPLC), powder

Sigma-Aldrich

R2625

Retinoic acid

David Holthoewer et al.
Neuro-degenerative diseases, 10(1-4), 224-228 (2012-02-04)
ADAM10 (a disintegrin and metalloproteinase 10) has been demonstrated to act as the main physiological α-secretase. Enzymatic activity of the α-secretase on the one hand prevents the formation of toxic Aβ peptides and on the other hand promotes the secretion
Vincenzo Bettoli et al.
The Journal of dermatological treatment, 24(3), 235-237 (2012-11-15)
The chemoprevention refers to the use of various types of chemical agents for preventing carcinogenic progression. Systemic retinoids are the most studied chemopreventive agents due to their capacity to regulate cell proliferation and their demonstrated efficacy in several clinical studies.
Systemic retinoid therapy for chemoprevention of nonmelanoma skin cancer in a patient treated with vemurafenib.
Rachael Anforth et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 30(19), e165-e167 (2012-06-06)
Frank Tippmann et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 23(6), 1643-1654 (2009-01-16)
Late-onset Alzheimer's disease is often connected with nutritional misbalance, such as enhanced cholesterol intake, deficiency in polyunsaturated fatty acids, or hypovitaminosis. The alpha-secretase ADAM10 has been found to be regulated by retinoic acid, the bioreactive metabolite of vitamin A. Here
Justin Cheeley et al.
Journal of the American Academy of Dermatology, 68(2), 247-254 (2012-08-25)
Bexarotene is the only Food and Drug Administration-approved retinoid for the treatment of cutaneous T-cell lymphoma (CTCL) and is associated with a relatively high frequency of adverse effects. Acitretin has anecdotally been reported to be effective for CTCL. We sought

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