Lithocholsure

Lithocolic acid · Lithocholate · (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid · 3-HYDROXYCHOLANIC ACID · 17-beta-(1-Methyl-3-carboxypropyl)ethiocholan-3-alpha-ol · NCI-C03861 · 3α-Hydroxy-5β-cholan-24-oic acid · NCI-CO-3861

https://huagongshe.com/de/chemical/9903

Identifikatoren & physikalische Daten

CAS No.	434-13-9
Summenformel	C24H40O3
Durchschnittliche Molmasse	376,6 g/mol
Monoisotopische Masse	376,29774514 g/mol
SMILES	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey	SMEROWZSTRWXGI-HVATVPOCSA-N
PubChem CID	9903
ChEMBL	CHEMBL1478
ChEBI	CHEBI:16325
EC No.	207-099-1
DTXSID	DTXSID6020779
Lokaler Name	Lithocholsure

Chemische & physikalische Eigenschaften

XLogP	6,3
Polarare Oberfläche (TPSA)	57,5
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	4
Schwere Atome	27
Formalladung	0
Komplexität	574
Stoffklassen	Bile Acids -> Quant Bile Acids
Arzneimittel	Pharmaceuticals -> Metabolite of Ursodeoxycholic acid
Lipide	Lipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]
Color/Form	HEXAGONAL LEAFLETS FROM ALC, PRISMS FROM ACETIC ACID
Löslichkeit	less than 1 mg/mL at 67.5 °F (NTP, 1992)FREELY SOL IN HOT ALCMORE SOL IN BENZENE THAN DESOXYCHOLIC ACIDINSOL IN PETROLEUM ETHER, GASOLINE, WATERSLIGHTLY SOL IN GLACIAL ACETIC ACID (ABOUT 0.2 G IN 3 ML)MORE SOL IN ETHER THAN CHOLIC OR DESOXYCHOLIC ACIDSOL IN ABOUT 10 TIMES ITS WT OF ETHYL ACETATEIn water, 0.38 mg/l at 25 °C.0.000377 mg/mLChloroform (Slightly), Dichloromethane (Slightly, Heated), DMSO (Slightly, Heated)18.83ug/L(25 ºC)
Decomposition	When heated to decomposition it emits acrid smoke and irritating fumes.
Schmelzpunkt	363 to 367 °F (NTP, 1992)184-186 °C183-188 °C (lit.)
Optical Rotation	SPECIFIC OPTICAL ROTATION: +33.7 DEG @ 20 °C/D (ABS ETHANOL, 1.5%)+23.3 DEG @ 19 °C/D+32.1 DEG @ 20 °C/D
Physical Description	Hexagonal leaflets (from alcohols) or prisms (from acetic acid) or white powder. (NTP, 1992)Solid
Collision Cross Section	203.0 Å² [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID6020779]200.33 Å² [M-H]- [CCS Type: DTMethod: stepped-field]199.95 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]198.8 Å² [M+HCOO]- [CCS Type: DTMethod: single field calibrated]203.1 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]210.8 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Other Experimental Properties	CRYSTALS /ETHYL ESTER/CRYSTALS /BENZYL ESTER/CRYSTALS /ACETYLLITHOCHOLIC ACID/FLAT NEEDLES FROM PENTANE /ACETYLLITHOCHOLIC ACID METHYL ESTER/For more Other Experimental Properties (Complete) data for LITHOCHOLIC ACID (6 total), please visit the HSDB record page.
Siedepunkt	445.09°C (rough estimate)
Dichte	1.0454 (rough estimate)
Brechungsindex	35.5 ° (C=1, EtOH)
Flammpunkt	9℃
Lagerbedingungen	room temp
pKa (Säurekonstante)	4.76±0.10(Predicted)
Aggregatzustand	Powder
Farbe	White to off-white
Biologische Quelle	bovine bilesynthetic
Merck	5545
BRN	3217757
InChIKey	SMEROWZSTRWXGI-HVATVPOCSA-N
SMILES	[H][C@]12CC[C@@]3([H])[C@]4([H])CC[C@H]([C@H](C)CCC(O)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2
LogP (Verteilungskoeffizient)	6.700 (est)
CAS Datenbank	434-13-9(CAS DataBase Reference)
EPA chemische Informationen	Lithocholic acid (434-13-9)

Sicherheit & Vorschriften

GHS-Einstufung	This chemical does not meet GHS hazard criteria for 42.9% (3 of 7) of reports.WarningH315 (57.1%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 7 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Brandgefahren	Flash point data for this compound are not available. It is probably combustible. (NTP, 1992)
Gesundheitsgefahren	ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and fumes. (NTP, 1992)
Reaktive Gruppe	Acids, Carboxylic
Special Reports	DHEW/NCIBioassay of Lithocholic Acid for Possible Carcinogenicity (1979) Technical Rpt Series No. 179 DHEW Pub No. (NIH) 79-1731
Air and Water Reactions	Insoluble in water.
Hazard Classes and Categories	Skin Irrit. 2 (57.1%)
Brandbekämpfung	Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Erste Hilfe	EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Freisetung ohne Brand	SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Anwendungen & Verwendung

Verwenden

Lithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. It has also been used in a study to investigate the regulation of hepatic phospholipid and bile acid homeostasis through SMAD3 activation by TGFβ.