(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

• ChemBase ID: 405
• Molecular Formular: C20H28O2
• Molecular Mass: 300.43512
• Monoisotopic Mass: 300.20893014
• SMILES: OC(=O)/C=C(/C=C/C=C(\C=C\C1=C(CCCC1(C)C)C)/C)\C
• Canonical SMILES: C/C(=C/C=C/C(=C/C(=O)O)/C)/C=C/C1=C(C)CCCC1(C)C
• InChI: InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
• InChIKey: SHGAZHPCJJPHSC-ZVCIMWCZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: alitretinoin
• Brand Name: Panretin; Panretin Gel; Panretyn; Panrexin; Renova; Retin-A; Retin-A Micro; Vesanoid
• Synonyms: Retinoic Acid; ALRT-1057; BAL4079; alitretinoin; 9-cis-Retinoic acid; Alitretinoin; (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic Acid; AGN 192013; ALRT 1057; LG 100057; LGD 100057; LGD 1057; NSC 659772; Panretin; Panretyn; Panrexin; 9-cis-Retinoic Acid; 9-cis-Tretinoin; 9-cis-Retinoic acid; 9-顺式维甲酸; 9-顺式视黄酸

Database IDs

• CAS Number: 5300-03-8
• MDL Number: MFCD00270072
• PubChem SID: 24899373; 160963868
• PubChem CID: 449171

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.996648
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.392896
• LogD (pH = 7.4): 2.6406298
• Log P: 5.0143676
• Molar Refractivity: 97.7908 cm^3
• Polarizability: 36.17498 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.66
• LOG S: -4.8
• Solubility (Water): 4.77e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.6 mg/L; Dimethyl Sulfoxide (25mg/ml); Ethanol (25 mg/ml)
• Apperance: Pale Yellow Solid
• Melting Point: 189-191°C
• Hydrophobicity(logP): 4.2

Safety Information

• Storage Condition: Amber Vial, -86°C Freezer
• Storage Warning: Store Dry in Freezer at -20°C for up to 1 year; in Solution
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61-36/37/38
• Safety Statements: 53-26-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335-H360
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313
• 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
• Storage Temperature: -20°C

Pharmacology Properties

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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H28O2

DETAILS

DrugBank - DB00523

• Drug Groups: approved; investigational
• Description: An important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth; and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). [PubChem]
• Indication: For topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma.
• Pharmacology: Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - R4643

Packaging
Sealed ampule
Biochem/physiol Actions
Ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR) that act as transcription factors to regulate the growth and differentiation of normal and malignant cells.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R4643.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - R245000

An endogenous retinoic acid isomer, which is capable of binding to both retinoic acid receptors (RAR) and retinoid X receptors (RXR). A biologically active ligand for members of the RAR and RXR subfamilies, implying that it may play a critical role in r

REFERENCES

• Allenby, G., et al.: Proc. Natl. Acad. Sci. U.S.A., 90, 30 (1993)
• Heyman, R.A., et al.: Cell, 68, 397 (1992)
• Levin, A.A., et al.: Nature, 355, 359 (1992)