4-{4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl}pentanoic acid

HCID 5645CAS 347841-46-7

Basic information

Standard SMILES
CC(CCC(=O)O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C
InChIKey
RUDATBOHQWOJDD-UHFFFAOYSA-N
Molecular formula
C24H40O4
Average molar mass
392.6 g/mol

Overview

See also: Ursodeoxycholic Acid (annotation moved to); 3,7-Dihydroxycholan-24-oic acid (annotation moved to).

Names & identifiers

Preferred name
4-{4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl}pentanoic acid
IUPAC
4-(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
English name
Ursodeoxycholic-2,2,4,4-d4 acid
Molecular formula
C24H40O4
Molecular weight
392.58

Names & synonyms

Urosodeoxycholic Acid EP Impurity KDeoxychenocholic acidcholan-24-oic acid, 3,7-dihydroxy-7-beta-Hydroxylithocholic acid(4R)-4-[(3S,5S,7S,8S,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]PENTANOIC ACID4-{4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl}pentanoic acidAllo-UDCA?Oprea1_287603SCHEMBL14845504HMS5079B06HMS5080C15347841-46-7
Show more names
Ursodeoxycholic-d4 AcidD4-Ursodeoxycholic Acid2H4]-Ursodeoxycholic AcidUrsodeoxycholic acid-2,2,4,4-d4Ursodeoxycholic-2,2,4,4-d4 acidUrosodeoxycholic Acid Impurity 28Ursodeoxycholic Acid-D4 (Standard)Ursodeoxycholic acid-[d4] (Solution)Ursodiol-d4 (Ursodeoxycholic Acid-d4)Ursodeoxycholic Acid-2,2,4,4-d4 (Major)
AAA56624ALBB-025013CCA84012EBC-69044s1643STL372965AKOS015998293ST013857

Database identifiers

CAS
347841-46-7
PubChem CID
5645
EC Number
110-134-2

Properties

Computed structural properties

XLogP
4.9
Topological polar surface area
77.8 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
28

Experimental & physicochemical properties

DrugsPharmaceuticals

Physicochemical properties

storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility
DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly),
form
Solid
color
White to Off-White
Stability
Hygroscopic
UNSPSC Code
12352211 · 12352211

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk
WGK 2
Signal word
Danger
Symbol(GHS)
GHS02,GHS06,GHS08
Storage Class
3 - Flammable liquids
target organs
Eyes
Hazard statements
H225-H301+H311+H331-H370

Chemistry & industry

Applications · 2 items

DescriptionUrsodeoxycholic acid-d4 (UDCA-d4) is intended for use as an internal standard for the quantification of UDCA (Item No. 15121) by GC- or LC-MS. UDCA is a secondary bile acid formed via epimerization of chenodeoxycholic acid (CDCA; ). UDCA is also a metabolite of lithocholic acid (LCA; ) in human liver microsomes. It inhibits taurocholic acid uptake in HeLa cells expressing recombinant sodium/taurocholate cotransporting polypeptide (NTCP) with an IC50 value of 3.6 μM. UDCA (50 μM) inhibits apoptosis induced by deoxycholic acid (DCA; Item Nos. 20756 | 18231) or ethanol in primary rat hepatocytes. Dietary administration of UDCA blocks DCA-induced increases in the number of TUNEL-positive hepatocytes in rats. Formulations containing UDCA have been used in the treatment of primary biliary cirrhosis.

UsesUrsodeoxycholic Acid-d4 is a deuterated form of Ursodeoxcholic Acid (U850000), which is used as an anticholelithogenic. Ursodeoxcholic Acid is an epimer with Chenodiol with respect to the hydroxyl group at C7. Ursodeoxycholic Acid-d4 was used as an internal standard for rapid quantification of bile acids by liquid chromatography-tandem mass spectrometry.

Suppliers35 total

盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]

Related reactions

2 records

Linked notes

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