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44707

Sigma-Aldrich

Acitretin

≥98.0% (HPLC)

Synonym(s):

9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

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About This Item

Empirical Formula (Hill Notation):
C21H26O3
CAS Number:
55079-83-9
Molecular Weight:
326.43
EC Number:
259-474-4
MDL number:
MFCD00866632
UNSPSC Code:
41116107
PubChem Substance ID:
57650239
NACRES:
NA.25

Quality Level

100

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

Gene Information

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

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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).

Signal Word

Danger

Hazard Statements

H315 - H319 - H360 - H410

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Sandra Philipp et al.
Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG, 10(11), 821-837 (2012-09-01)
Monotherapy with TNF-α inhibitors does not always produce a sufficient response in psoriasis patients. Combinations of TNF-α antagonists such as adalimumab with systemic antipsoriatic therapies such as methotrexate are not approved for use in psoriasis, and the published data are
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
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.
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
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