- 9-cis-Retinoic Acid
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- $30.00
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2025-06-27
- CAS:5300-03-8
- Min. Order: 50KG
- Purity: 99%
- Supply Ability: 500000kg
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| | 9-CIS-RETINOIC ACID Basic information |
| Product Name: | 9-CIS-RETINOIC ACID | | Synonyms: | RETINOIC ACID, 9-CIS-;RARECHEM AL BE 0738;(2E,4E,6Z,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYLCYCLOHEX-1-ENYL)NONA-2,4,6,8-TETRAENOIC ACID;9-CIS-RETINOIC ACID;9-CIS-TRETINOIN;Tretinoin EP Impurity D;(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex;Isotretinoin Impurity 4（Isotretinoin EP Impurity D） | | CAS: | 5300-03-8 | | MF: | C20H28O2 | | MW: | 300.44 | | EINECS: | 1533716-785-6 | | Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids | | Mol File: | 5300-03-8.mol |  |
| | 9-CIS-RETINOIC ACID Chemical Properties |
| Melting point | 189-191°C | | Boiling point | 462.8±14.0 °C(Predicted) | | density | 1.011±0.06 g/cm3(Predicted) | | RTECS | VH6450000 | | storage temp. | -20°C | | solubility | Acetonitrile (Very Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol ( | | pka | 4.73±0.33(Predicted) | | form | Light yellow to orange crystalline powder. | | color | Pale Yellow to Yellow | | biological source | natural | | Water Solubility | Soluble in chloroform (50 mg/ml), DMSO (~25 mg/ml), ethanol (25 mg/ml), and acetone (25 mg/ml). Insoluble in water. | | Sensitive | Moisture & Light Sensitive | | Stability: | Store Dry in Freezer at -20°C for up to 1 year; in Solution at -20°C for up to 3 Months. | | 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 | | SMILES | C(O)(=O)/C=C(/C=C/C=C(\C=C\C1C(C)(C)CCCC=1C)/C)\C | | CAS DataBase Reference | 5300-03-8(CAS DataBase Reference) |
| Hazard Codes | T | | Risk Statements | 61-36/37/38 | | Safety Statements | 53-26-36/37/39-45 | | WGK Germany | 3 | | HS Code | 29162090 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Eye Irrit. 2
Repr. 1B
Skin Irrit. 2
STOT SE 3 | | Hazardous Substances Data | 5300-03-8(Hazardous Substances Data) |
| | 9-CIS-RETINOIC ACID Usage And Synthesis |
| Description | Alitretinoin was introduced in the US for the topical treatment of
cutaneous lesions in patients with Kaposi's sarcoma (KS), the most frequent
malignancy observed in AIDS patients. It is a derivative of 9-cis-retinoic acid (9-
cis-RA) identified as an endogenous hormone in mammalian tissues. Alitretinoin
binds to all isoforms of the intracellular retinoid X (RXR) and retinoid A (RAR)
receptors thus inducing cell differentiation, increasing cell apoptosis and
inhibiting cellular proliferation in experimental models of human cancer. In an
international phase III trial in patients with KS, 42% of 82 patients treated with
0.1% gel formulation experienced complete or partial responses cf 7% for
controls. Alitretinoin is the first topical therapy for KS and is expected to be a
new option to its traditional management. | | Chemical Properties | Pale Yellow Solid | | Originator | Ligand (US) | | Uses | 9-cis-Retinoic acid is a vitamin A analog that inhibits cell proliferation and induces cell differentiation. 9-cis-Retinoic acid is an inhibitor of Cox-2 and an activator of RAR α, RAR β, RAR γ and RXR. | | Uses | 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 regulating retinoid-responsive pathways. | | Definition | ChEBI: A retinoic acid in which the exocyclic double bonds have 7E,9Z,11E,13E geometry. | | Indications | Alitretinoin (Panretin) is a naturally occurring endogenous
retinoid that binds to and activates all known
retinoid receptors (both RARs and RXRs). It is approved
for the topical treatment of cutaneous lesions of
Kaposi’s sarcoma. Most patients have local irritation
while using alitretinoin gel; however, the irritation
rarely necessitates discontinuation of therapy. | | Brand name | Panretin (Ligand). | | 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. | | Synthesis | Preparation of isotretinoin EP impurity D (compound of formula I): under the protection of nitrogen, add 2L of ethanol and 100g of all-trans retinoic acid to the reaction flask with stirring, and then increase the temperature to 50-55 , add PdCl289mg. 1.5h after the reaction, the purity of the product was 21% by HPLC. The reaction solution was slowly cooled down to 0~5C, held for 180 min, and filtered; the filtrate was added into another clean reaction flask, and continued to be cooled down to -10~-6C, held for 20 min, and filtered, to obtain the product isotretinoin EP impurity D 12.1g, with a total yield of 12.1%, and a purity of 99.60% by HPLC. Allelvic acid can be obtained from all-trans retinoic acid as raw material in common industrial-grade organic solvents using palladium compound catalysis. The method is easy to operate, low cost, controlled conditions, and convenient for industrial production; after the post-processing step, alevetic acid with a purity of more than 99% can be obtained, and the product yield reaches more than 12%, which has high application value.
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| | 9-CIS-RETINOIC ACID Preparation Products And Raw materials |
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