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Home> Encyclopedia >   /  Organic Intermediate  /  Pharmaceutical Intermediates  /  Antibiotic and antimicrobial agents
9-CIS-RETINOIC ACID structure
9-CIS-RETINOIC ACID structure

9-CIS-RETINOIC ACID

Iupac Name:(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
CAS No.: 5300-03-8
Molecular Weight:300.442
Modify Date.: 2022-11-01 09:00
Introduction: Alitretinoin was introduced in the US for the topical treatment ofcutaneous lesions in patients with Kaposi's sarcoma (KS), the most frequentmalignancy observed in AIDS patients. It is a derivative of 9-cis-retinoic acid (9-cis-RA) identified as an endogenous hormone in mammalian tissues. Alitretinoinbinds to all isoforms of the intracellular retinoid X (RXR) and retinoid A (RAR)receptors thus inducing cell differentiation, increasing cell apoptosis andinhibiting cellular proliferation in experimental models of human cancer. In aninternational phase III trial in patients with KS, 42% of 82 patients treated with0.1% gel formulation experienced complete or partial responses cf 7% forcontrols. Alitretinoin is the first topical therapy for KS and is expected to be anew option to its traditional management. View more+
1. Names and Identifiers
1.1 Name
9-CIS-RETINOIC ACID
1.2 Synonyms

(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid (2E,4E,6Z,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYLCYCLOHEX-1-ENYL)NONA-2,4,6,8-TETRAENOIC ACID (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid (9cis)-Retinoic acid 9(Z)-Retinoic acid 9-cis Retinoic Acid 9-CIS-TRETINOIN 9-cis-Tretinoin,Alitretinoin 9Z-retinoic acid Alitretinoin Isotretinoin Impurity 4(Isotretinoin EP Impurity D) MFCD00270072 Panretin Gel RARECHEM AL BE 0738 Retinoic acid, (9cis)- RETINOIC ACID, 9-CIS- Tretinoin EP Impurity D

1.3 CAS No.
5300-03-8
1.4 CID
449171
1.5 EINECS(EC#)
610-929-9
1.6 Molecular Formula
C20H28O2 (isomer)
1.7 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+
1.8 InChkey
SHGAZHPCJJPHSC-ZVCIMWCZSA-N
1.9 Canonical Smiles
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
1.10 Isomers Smiles
CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C
2. Properties
3.1 Density
1.011
3.1 Melting point
189-191°C
3.1 Boiling point
462.8 °C at 760 mmHg
3.1 Refractive index
1.556
3.1 Flash Point
462.8 °C at 760 mmHg
3.1 Precise Quality
300.20900
3.1 PSA
37.30000
3.1 logP
5.60260
3.1 Appearance
Pale yellow solid
3.2 Storage
Store at -20°C. Moisture Sensitive. Light Sensitive. Store under Nitrogen.
3.3 Chemical Properties
Pale Yellow Solid
3.4 Color/Form
Yellow to light-orange crystalline powder
Crystals from ethanol
3.5 Physical
Solid
3.6 pKa
4.73±0.33(Predicted)
3.7 Water Solubility
Soluble in DMSO; slightly soluble in polyethylene glycol 400, octanol, ethanol; practically insoluble in water, glycerin
... Soluble in ether; slightly soluble in ... chloroform.
3.8 Spectral Properties
Max absorption (methanol): 351 nm (Epsilon=45,000)
3.9 Stability
Store Dry in Freezer at -20°C for up to 1 year; in Solution at -20°C for up to 3 Months.
3.10 StorageTemp
-20°C
3. Use and Manufacturing
4.1 Definition
ChEBI: A retinoic acid in which the exocyclic double bonds have 7E,9Z,11E,13E geometry.
4.2 GHS Classification
Signal: Warning
GHS Hazard Statements
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes
P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P321, P330, P332+P313, P337+P313, P362, P391, P405, and P501
4.3 Usage
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.
4. Safety and Handling
5.1 Symbol
GHS07, GHS08
5.1 Hazard Codes
T
5.1 Signal Word
Danger
5.1 Risk Statements
R36/37/38;R61
5.1 Safety Statements
S26;S36/37/39;S45;S53
5.1 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl tretinoin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
5.2 Octanol/Water Partition Coefficient
log Kow = 6.30
5.3 Hazard Declaration
H315-H319-H335-H360
5.3 DisposalMethods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
5.4 RIDADR
NONH for all modes of transport
5.4 Caution Statement
P201-P261-P305 + P351 + P338-P308 + P313
5.4 Formulations/Preparations
Topical: Powder (available by nonproprietary name); Cream: 0.02% Renova Emollient (with methylparaben), (OrthoNeutrogena);0.025% Avita (Bertek), Retin-A (OrthoNeutrogena); 0.05% Renova Emollient (with methylparaben) (OrthoNeutrogena), Retin-A (OrthoNeutrogena), 0.1% Retin-A (OrthoNeutrogena). Gel: 0.01% Retin-A (with denatured alcohol 90% and butylated hydroxytoluene) (OrthoNeutrogena, 0.025% Avita (Bertek), Retin-A (with denatured alcohol 90% and butylated bydroxytoluene) (OrthoNeutrogena). Gel (containing nicrospheres): 0.04% Retin-A Micro (with benzyl alcohol and propylene glycol) (OrthoNeutrogena), 0.1% Retin-A Micro with benzyl alcohol and propylene glycol) (OrthoNeutrogena). Solution: 0.05% Retin-A (with denatured alcohol 55%, butylated hydroxytoluene, and polyethylene glycol 400) (OrthoNeutrogena).
Oral: Capsules: 10 mg Vesanoid (with methylparaben and propylparaben), (Roche).
TRETINOIN, USP (ALL-TRANS-RETINOIC ACID; (RETIN-A), LIQUID CREAM (0.025 TO 0.1%), & A GEL (0.025% & 0.01%).
5.5 WGK Germany
3
5.5 RTECS
VH6450000
5.5 Safety
Hazard Codes:T
Risk Statements:61-36/37/38
61:May cause harm to the unborn child
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:53-26-36/37/39-45
53:Avoid exposure - obtain special instruction before use
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
WGK Germany:3
5.6 Specification

The 9-cis-Retinoic acid with the cas number 5300-03-8 is also called Retinoicacid, cis-9,trans-13- (8CI). The IUPAC name is(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid. Its molecular formula is C20H28O2. This chemical belongs to the following product categories: (1)Retinoids; (2)Pharmaceuticals. It should be stored at −20°C. 

The properties of the chemical are: (1)ACD/LogP: 6.83; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.94; (4)ACD/LogD (pH 7.4): 4.14; (5)ACD/BCF (pH 5.5): 11810.57; (6)ACD/BCF (pH 7.4): 186.43; (7)ACD/KOC (pH 5.5): 15995.9; (8)ACD/KOC (pH 7.4): 252.49; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.556; (14)Molar Refractivity: 95.52 cm3; (15)Molar Volume: 297.1 cm3; (16)Polarizability: 37.87×10-24cm3; (17)Surface Tension: 39.1 dyne/cm; (18)Enthalpy of Vaporization: 79.32 kJ/mol; (19)Vapour Pressure: 7.55×10-10 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following: (1)Irritating to eyes, respiratory system and skin; (2)May cause harm to the unborn child; (3)In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; (4)Wear suitable protective clothing, gloves and eye/face protection; (5)In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.); (6)Avoid exposure - obtain special instructions before use.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)\C=C(\C=C\C=C(\C=C\C1=C(\CCCC1(C)C)C)C)C
(2)InChI: InChI=1/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+
(3)InChIKey: SHGAZHPCJJPHSC-YCNIQYBTBL

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

H360 May damage fertility or the unborn child

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. Other Information
6.0 Usage
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.
6.1 Cell Line:
CA 9-22 and NA cells
6.2 Concentration:
1 μM, 10 μM
6.3 Incubation Time:
0 day, 1 day, 3 days, 5 days
6.4 Result:
Significantly decreased proliferation.
6.5 Animal Model:
Male C57BL/6J mice (6-8 weeks; 19-22 g) treatment with bile duct ligated
6.6 Dosage:
1 mg/kg
6.7 Administration:
Intravenous injection; daily; for 10 days
6.8 Result:
Significantly decreased the serum ALT and AST level, alleviated hepatic necrosis.
6.9 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.
6.10 Chemical Properties
Pale Yellow Solid
6.11 Originator
Ligand (US)
6.12 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.
6.13 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.
6.14 Definition
ChEBI: A retinoic acid in which the exocyclic double bonds have 7E,9Z,11E,13E geometry.
6.15 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.
6.16 Brand name
Panretin (Ligand).
6.17 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.
7. Computational chemical data
  • Molecular Weight: 300.442g/mol
  • Molecular Formula: C20H28O2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 300.208930132
  • Monoisotopic Mass: 300.208930132
  • Complexity: 567
  • Rotatable Bond Count: 5
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 37.3
  • Heavy Atom Count: 22
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 4
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceB4MAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAGgAACAAADgCAgAACCAAAAgCIAiDSCAAAAAAgAAAICAAAAEgIBAIAAQAAEAAAgAAIkQMAgMAPAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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