Acitretin EP Impurity A (Acitretin USP Related Compound A, 13-cis-Acitretin)

Basic Information

View in Editor

CAS Number

69427-46-9

Molecular Formula

C21H26O3

Molecular Weight

326.44 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

190-193°C

SMILES

View in Editor

CC1=CC(=C(C(=C1C=CC(=CC=CC(=CC(=O)O)C)C)C)C)OC

InChI

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+

InChIKey

IHUNBGSDBOWDMA-AQFIFDHZSA-N

LogP

5.167060000000005

Topological Polar Surface Area

46.53 Å²

Hydrogen Bond Donor/Acceptor

1 / 3

Complexity

539

Synonyms & References

English

BK59Y5A02O
SCHEMBL159360
13-cis Acitretin
(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Isoacitretin
CHEBI:50174
ACITRETIN IMPURITY A [EP IMPURITY]
9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4, USP Acitretin Related Compound A,6,8-nonatetraenoic Acid, 13-cis-Etretin, Isoacitretin, Isoetretin, Ro 13-7652
UNII-BK59Y5A02O
NCGC00188949-01
2,4,6,8-Nonatetraenoicacid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, (2Z,4E,6E,8E)-
AKOS037515335
13-cis-Etretin
2Z-acitretin
2,4,6,8-Noneatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, (Z,E,E,E)-
IHUNBGSDBOWDMA-UGOGCBOOSA-N
2,4,6,8-NONATETRAENOIC ACID, 9-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-3,7-DIMETHYL-, (2Z,4E,6E,8E)-
Ro-13-7652
Q27121938
69427-46-9
Isoetretin
Ro 13-7652
DTXSID901316817
Acetretin
13-cis-Acitretin
(all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid
2-amino-9-(4-isopropyl-phenyl)-1,9-dihydro-purin-6-one
9-(4-Isopropyl-phenyl)-guanin
9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid
9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid
SNGP-201-04-E06

MDL Number

MFCD00870444

FAQ

What are the physical and chemical properties of Acitretin EP Impurity A (CAS: 69427-46-9)?

Acitretin EP Impurity A, also known as Acitretin USP Related Compound A or 13-cis-Acitretin (CAS: 69427-46-9), is a crystalline compound with a molecular weight of approximately 314.37 g/mol. It has a low solubility in water but is more soluble in organic solvents like ethanol and methanol. Chemically, it is relatively stable under normal conditions but can react with strong acids and bases. It is important for pharmaceutical applications due to its structural similarities to the main compound, acitretin.

How is Acitretin EP Impurity A (CAS: 69427-46-9) typically synthesized?

Acitretin EP Impurity A is typically synthesized via a stereocontrolled pathway that involves the transformation of acitretin into its 13-cis isomer. This process often utilizes chiral catalysts to ensure high stereoselectivity. The synthesis usually involves protecting groups, hydrolysis, and reductive amination steps. The overall yield is around 70-80%, making it a feasible and industrially viable process.

What industries use Acitretin EP Impurity A (CAS: 69427-46-9)?

Acitretin EP Impurity A (CAS: 69427-46-9) is primarily used in the pharmaceutical industry. It is a key intermediate in the synthesis of acitretin, a drug used to treat psoriasis. While it is not directly used in other industries like polymers or semiconductors, its structural similarity to acitretin makes it valuable for research and development in dermatological treatments.

What precautions should be taken when handling Acitretin EP Impurity A (CAS: 69427-46-9)?

When handling Acitretin EP Impurity A (CAS: 69427-46-9), it is crucial to take appropriate safety measures. Always work in a well-ventilated area or fume hood to avoid inhalation of dust or vapors. Use gloves and safety goggles to protect your skin and eyes. It is also recommended to wear a lab coat and follow standard laboratory hygiene practices. Always consult the Safety Data Sheet (SDS) for detailed handling instructions and emergency procedures.