Ursodeoxycholic acid

Iupac Name：(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid

CAS No.: 128-13-2

Molecular Weight：392.572

Modify Date.: 2022-11-05 19:40

Introduction: Ursodiol reduces cholesterol absorption and is used to dissolve gallstones.Target: OthersUrsodiol, also known as ursodeoxycholic acid and the abbreviation UDCA, is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery. The drug is very expensive, however, and if the patient stops taking it, the gallstones tend to recur i View more+

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1. Names and Identifiers

1.1 Name: Ursodeoxycholic acid
1.2 Synonyms: (3α,5β,7β)-3,7-Dihydroxycholan-24-oic acid (4R)-4-[(3R,5S,7S,8R,9S,10R,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate 17β-(1-Methyl-3-carboxypropyl)etiocholane-3α,7β-diol 3α,7β-Dihydroxy-5β-cholan-24-oate 3α,7β-Dihydroxy-5β-cholan-24-oic acid 3α,7β-Dihydroxy-5β-cholanic acid 3α,7β-Dihydroxy-5β-cholanoic acid 3α,7β-Dihydroxycholanic acid 5.beta.-Chol-24-oic acid-3.alpha., 7.beta.-diol 5β-Cholan-24-oic acid, 3α,7β-dihydroxy- 5β-Cholanic acid, 3α,7β-dihydroxy- 7beta-Hydroxylithocholic acid 7β-Hydroxylithocholic acid Actigall Adursal Antigall Antigall (TN) Arsacol Cholan-24-oic acid, 3,7-dihydroxy-, (3-.alpha.,5-.beta., 7-.beta.)- Cholan-24-oic acid, 3,7-dihydroxy-, (3α,5β,7β)- Cholan-24-oic acid,3,7-dihydroxy-,(3R,5a,- 7a)- Cholit-Ursan Delursan deoxy- Desocol Desol Destolit Deursil Litursol Lyeton NSC 683769 Paptarom Solutrat UDCA Urdes Urosiol Ursacol Ursic acid Urso Urso (TN) Urso Deoxy Cholic Acid Ursobilin Ursochol Ursocholic acid, deoxy- Ursocol Ursodamor Ursodeoxycholic acid (JP14) Ursodeoxycholoc acid Ursodesoxycholic acid Ursodiol Ursodiol (USP) Ursofalk Ursogall Ursolvan Ursosan

1.3 CAS No.: 128-13-2

1.4 CID: 31401

1.5 EINECS(EC#): 204-879-3

1.6 Molecular Formula: C24H40O4 (isomer)

1.7 Inchi: InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1

1.8 InChkey: RUDATBOHQWOJDD-UZVSRGJWSA-N

1.9 Canonical Smiles: CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C

1.10 Isomers Smiles: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C

2. Properties

2.1 Density: 1.128

2.1 Melting point: 203-206℃

2.1 Boiling point: 547.1 °C at 760mmHg

2.1 Refractive index: 60.5 ° (C=2, EtOH)

2.1 Flash Point: 298.8 °C

2.1 Precise Quality: 392.29300

2.1 PSA: 77.76000

2.1 logP: 4.47790

2.1 Solubility: ethanol: 50?mg/mL, clear

2.2 Appearance: white crystalline powder

2.3 Storage: Ambient temperatures.

2.4 Color/Form: Powder

2.5 pKa: pKa 5.04±0.04(H2Ot = 25.0±0.1I = 0.00)(Approximate)

2.6 Water Solubility: practically insoluble in water

2.7 Stability: Stable under normal temperatures and pressures.

2.8 StorageTemp: Store in a tightly closed container. Store in a cool, dry area away from incompatible substances.

3. Use and Manufacturing

3.1 Definition: ChEBI: A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.

3.2 Produe Method

3.3 Purification Methods: Recrystallise ursodiol from wet Et2O, EtOH or EtOH/MeOH. [Iwasaki Hoppe Seyler's Z Physiol Chem 244 181, 183 1936, Beilstein 10 III 1635.] Ursodeoxycholic acid Preparation Products And Raw materials Raw materials

3.4 Usage: Used as an anticholelithogenic

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S24/25

4.1 RIDADR: 25kgs

4.1 WGK Germany: 2

4.1 RTECS: FZ2000000

4.1 Safety: Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26?
S24/25:Avoid contact with skin and eyes.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: FZ2000000
F: 10
Poison by intraperitoneal and intravenous routes. Experimental teratogenic and reproductive effects. Mutation data reported. Stimulates the flow of bile to the duodenum (a cholagogic). When heated to decomposition it emits acrid smoke and irritating fumes.

4.2 Specification: ?Ursodeoxycholic acid (CAS NO.128-13-2) is also named as 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3-alpha,7-beta-diol ; 3,7-Dihydroxycholan-24-oic acid ; 3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid ; 3-alpha,7-beta-Dihydroxycholanic acid ; 3-alpha,7-beta-Dioxycholanic acid ; 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid ; 4-10-00-01604 (Beilstein Handbook Reference) ; 7-beta-Hydroxylithocholic acid ; Actigall ; Arsacol ; BRN 3219888 ; CCRIS 5502 ; Cholit-ursan ; Delursan ; Destolit ; Deursil ; Litursol ; Lyeton ; NSC 657950 ; NSC 683769 ; Peptarom ; Solutrat ; UNII-724L30Y2QR ; UrSO ; Ursacol ; Urso 250 ; Urso DS ; Urso Forte ; Ursobilin ; Ursochol ; Ursocholic acid, deoxy- ; Ursodamor ; Ursodeoxycholate ; Ursodiol ; Ursofalk ; Ursolvan .?Ursodeoxycholic acid (CAS NO.128-13-2) is white crystalline powder.

4.3 Toxicity

1.	???	mmo-sat 40?mg/L	???	MUREAV ?? Mutation Research. 158 (1985),45.
2.	???	orl-rat TDLo:11,900?mg/kg (4-20D preg):TER	???	AIPTAK ?? Archives Internationales de Pharmacodynamie et de Therapie. 246 (1980),149.
3.	???	orl-rat LD50:4600?mg/kg	???	BCFAAI ?? Bollettino Chimico Farmaceutico. 126 (1987),282.
4.	???	ipr-rat LD50:890?mg/kg	???	NIIRDN ?? “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),95.
5.	???	ivn-rat LD50:310?mg/kg	???	NIIRDN ?? “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),95.
6.	???	ivn-mus LD50:240?mg/kg	???	NIIRDN ?? “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),95.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
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.
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

7. Synthesis Route

128-13-2Total: 11 Synthesis Route

859-97-2 1 Suppliers

474-25-9 259 Suppliers

128-13-2 375 Suppliers

Literatures:
Tsukamoto Journal of Biochemistry (Tokyo, Japan), 1940 , vol. 32, p. 461,462
Yield: null

434-13-9 55 Suppliers

474-25-9 259 Suppliers

128-13-2 375 Suppliers

Literatures:
Kollerov; Monti; Deshcherevskaya; Lobastova; Ferrandi; Larovere; Gulevskaya; Riva; Donova Steroids, 2013 , vol. 78, # 3 p. 370 - 378
Yield: null

474-25-9 259 Suppliers

128-13-2 375 Suppliers

4651-67-6 100 Suppliers

Literatures:
Chemistry Letters, , # 7 p. 693 - 694
Yield: ~26%

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8. Other Information

8.0 Usage: A secondary bile acid

9. Computational chemical data

Molecular Weight: 392.572g/mol
Molecular Formula: C₂₄H₄₀O₄
Compound Is Canonicalized: True
XLogP3-AA: 4.9
Exact Mass: 392.29265975
Monoisotopic Mass: 392.29265975
Complexity: 605
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 77.8
Heavy Atom Count: 28
Defined Atom Stereocenter Count: 10
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4OAAAAAAAAAAAAAAAAAAAAYAAAAAwYMAAAAAAAGDAAAAAGgAACAAADxSggAICCAAAAgAIAACQCAAAAAAAAAAAAAEAAAAAEBIAAAAAQAAEAAAAAAGI6PSPgAAAAAAAAADAAAYAADAAAQAACAAAAA==

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