Home > Compound List > Compound details
55079-83-9 molecular structure
click picture or here to close

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

ChemBase ID: 72641
Molecular Formular: C21H26O3
Molecular Mass: 326.42934
Monoisotopic Mass: 326.18819469
SMILES and InChIs

SMILES:
c1c(c(c(c(c1C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C)C)OC
Canonical SMILES:
COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
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

Cite this record

CBID:72641 http://www.chembase.cn/molecule-72641.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
IUPAC Traditional name
acitretin
(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Synonyms
9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Acitretin
Soriatane
Acitretin
(all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid
Neotigason, Soriatane
Neotigason
Etretin
CAS Number
55079-83-9
EC Number
259-474-4
MDL Number
MFCD00866632
PubChem SID
24868318
162037566
PubChem CID
5284513

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 5.011076  H Acceptors
H Donor LogD (pH = 5.5) 4.976502 
LogD (pH = 7.4) 3.2266924  Log P 5.5870485 
Molar Refractivity 104.1665 cm3 Polarizability 38.030373 Å3
Polar Surface Area 46.53 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
Yellow Solid expand Show data source
Melting Point
215-218°C (dec.) expand Show data source
Storage Condition
-20°C expand Show data source
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
Toxic Toxic (T) expand Show data source
UN Number
3077 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
9 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
61-36/38-50/53 expand Show data source
Safety Statements
53-26-45-60-61 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H315-H319-H360-H410 expand Show data source
GHS Precautionary statements
P201-P273-P305 + P351 + P338-P308 + P313-P501 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 3077 9/PG 3 expand Show data source
Mechanism of Action
Second generation retinoid expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Active against epithelial tumours expand Show data source
Used for treatment of psoriasis, antineoplastic agent expand Show data source
Empirical Formula (Hill Notation)
C21H26O3 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S1368 external link
Research Area: Inflammation
Biological Activity:
Acitretin is a second generation retinoid. It is taken orally, and is typically used for psoriasis. It is a metabolite of etretinate, which was used prior to the introduction of acitretin. Etretinate was discontinued because it had a narrow therapeutic index as well as a long elimination half-life (t1/2=120 days), making dosing difficult. In contrast, acitretin’s half-life is approximately 2 days. [1]
Sigma Aldrich - 44707 external link
Biochem/physiol Actions
Synthetic retinoid that is a metabolite of etretinate. Preferentially binds to cellular retinoic acid binding proteins (CRABPs).
Toronto Research Chemicals - A189900 external link
A synthetic retinoid which is the major metabolite of etretinate (E938000).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Acitretin
  • • Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)
  • • Liu, X., et al.: Cancer Chemother. Pharmacol., 63, 167 (2008)
  • • Ger. Pat., 1977, 2 636 879; CA, 87, 23565y, (synth, deriv)
  • • Haenni, R. et al., Helv. Chim. Acta, 1977, 60, 2309, (synth, pmr, ms, metab)
  • • Mayer, H. et al., Experientia, 1978, 34, 1105, (rev, pharmacol)
  • • Englert, G. et al., Helv. Chim. Acta, 1978, 61, 2697, (pmr, isom)
  • • Paravicini, U. et al., Ann. N.Y. Acad. Sci., 1981, 359, 54, (rev, metab)
  • • Ward, A. et al., Drugs, 1983, 26, 9, (rev)
  • • Bestmann, H.J. et al., Annalen, 1984, 1740, (isoetretin)
  • • Cunliffe, W.J., Biochem. Soc. Trans., 1986, 14, 943, (props)
  • • Coffey, J.W. et al., Int. Congr. Ser. Excerpta Med., 1987, 750, 705, (rev, isomers)
  • • Jakobsen, P. et al., J. Chromatogr., 1987, 415, 413, (hplc)
  • • Pilkington, T. et al., Drugs, 1992, 43, 597, (rev)
  • • Bouvy, M.L. et al., Pharm. Weekbl., Sci. Ed., 1992, 14, 33, (Acitretin, rev, pharmacokinet)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 754; 758
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EMJ500; REP400
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle