Catalpol Chemical Properties

Melting point:

203-205°C

Boiling point:

675.6±55.0 °C(Predicted)

Density 

1.72±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)

form 

Solid

pka

12.79±0.70(Predicted)

color 

White to Off-White

InChI

InChI=1/C15H22O10/c16-3-6-9(19)10(20)11(21)14(23-6)24-13-7-5(1-2-22-13)8(18)12-15(7,4-17)25-12/h1-2,5-14,16-21H,3-4H2/t5-,6-,7-,8+,9-,10+,11-,12+,13+,14+,15-/s3

InChIKey

LHDWRKICQLTVDL-CLLMHHLUSA-N

SMILES

C([C@]12O[C@H]1[C@@H](O)[C@]1([H])C=CO[C@@H](O[C@@]3([H])[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@]21[H])O |&1:1,3,4,6,11,13,15,16,18,20,25,r|

LogP

-4.609 (est)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

LZ5776816

HS Code 

29389090

Toxicity

mouse,LD,intravenous,> 2500mg/kg (2500mg/kg),Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 93, 1968.

Catalpol Usage And Synthesis

Description

Catalpol is an iridoid glycoside that has been isolated from R. glutinosa and has diverse biological activities, including anti-apoptotic, pro-angiogenic, and radioprotective properties. It protects against mitochondrial pathway-dependent apoptosis in PC12 rat adrenal pheochromocytoma cells and H9c2 rat embryonic ventricular myocardial cells when used at a concentration of 10 μM. Catalpol pretreatment reduces apoptosis and improves viability in AHH-1 human lymphocyte cells exposed to ionizing radiation and reduces intestinal damage induced by radiation in mice when used at concentrations and doses ranging from of 25 to 100 μg/ml and 25 to 100 mg/kg, respectively. In a rat model of stroke, catalpol (5 mg/kg, i.p.) increases the expression of erythropoietin and VEGF and improves angiogenesis in the brain.

Chemical Properties

Light brown powder

Uses

Catapol is an iridoid glucoside that has been shown to alleviate neuropathic pain.

Definition

ChEBI: Catalpol is an organic molecular entity. It has a role as a metabolite.

in vivo

References

[1] YANJIE WANG. Simultaneous Determination of Catalpol, Aucubin, and Geniposidic Acid in Different Developmental Stages of Rehmannia glutinosa Leaves by High Performance Liquid Chromatography.[J]. Journal of Analytical Methods in Chemistry, 2016, 2016: 4956589. DOI: 10.1155/2016/4956589
[2] WENNA CHEN. Neuroprotective activities of catalpol against CaMKII-dependent apoptosis induced by LPS in PC12 cells[J]. British Journal of Pharmacology, 2013, 169 5: 1140-1152. DOI: 10.1111/bph.12200
[3] LING-AI HU. Catalpol inhibits apoptosis in hydrogen peroxide-induced cardiac myocytes through a mitochondrial-dependent caspase pathway.[J]. Bioscience Reports, 2016, 36 3. DOI: 10.1042/bsr20160132
[4] CHENGJIE CHEN. Radio-protective effect of catalpol in cultured cells and mice.[J]. Journal of Radiation Research, 2013, 54 1: 76-82. DOI: 10.1093/jrr/rrs080
[5] HUI-FENG ZHU. Catalpol increases brain angiogenesis and up-regulates VEGF and EPO in the rat after permanent middle cerebral artery occlusion.[J]. International Journal of Biological Sciences, 2010, 6 5: 443-453. DOI: 10.7150/ijbs.6.443

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