Catalpol

Modify Date: 2024-01-02 22:30:56

Catalpol Structure
Catalpol structure
 Common Name Catalpol
CAS Number 2415-24-9 Molecular Weight 362.329
Density 1.7±0.1 g/cm3 Boiling Point 675.6±55.0 °C at 760 mmHg
Molecular Formula C15H22O10 Melting Point 203-205ºC
MSDS Chinese USA Flash Point 362.4±31.5 °C

 Use of Catalpol


Catalpol, an iridoid glycoside, has neuroprotective, anti-inflammatory, and anti-hepatitis virus effects.IC50 Value:Target: neuroprotective, anti-inflammatory, and anti-hepatitis virus natural product.In vitro: Catalpol could be encapsulated into composite nanofibers and induce differentiation of hASCs into neural-like cells, which might offer new avenues in nerve regeneration [1].In vivo: The pharmacokinetics of catalpol in normal and doxorubicin-induced chronic kidney disease rats after oral administration of Rehmannia glutinosa extract was determined, and the extraction recoverie of catalpol was higher than 68.24% [2]. The protective effect of catalpol on renal IRI mice through suppressing phosphatidylinositol 3-kinase/protein kinase B (PI3K/Akt)-endothelial nitric oxide synthase (eNOS) and against inflammation, and the possible underlying mechanism [3].

 Names

Name Catalpol
Synonym More Synonyms

 Catalpol Biological Activity

Description Catalpol, an iridoid glycoside, has neuroprotective, anti-inflammatory, and anti-hepatitis virus effects.IC50 Value:Target: neuroprotective, anti-inflammatory, and anti-hepatitis virus natural product.In vitro: Catalpol could be encapsulated into composite nanofibers and induce differentiation of hASCs into neural-like cells, which might offer new avenues in nerve regeneration [1].In vivo: The pharmacokinetics of catalpol in normal and doxorubicin-induced chronic kidney disease rats after oral administration of Rehmannia glutinosa extract was determined, and the extraction recoverie of catalpol was higher than 68.24% [2]. The protective effect of catalpol on renal IRI mice through suppressing phosphatidylinositol 3-kinase/protein kinase B (PI3K/Akt)-endothelial nitric oxide synthase (eNOS) and against inflammation, and the possible underlying mechanism [3].
Related Catalog
References

[1]. Zhao M, et al.Comparative pharmacokinetics of catalpol and acteoside in normal and chronic kidney disease rats after oral administration of Rehmannia glutinosa extract. Biomed Chromatogr. 2015 May 29.

[2]. Guo JH, et al.Potential Neurogenesis of Human Adipose-Derived Stem Cells on Electrospun Catalpol-Loaded Composite Nanofibrous Scaffolds. Ann Biomed Eng. 2015 Mar 31.

[3]. Zhu J,Catalpol protects mice against renal ischemia/reperfusion injury via suppressing PI3K/Akt-eNOS signaling and inflammation. Int J Clin Exp Med. 2015 Feb 15;8(2):2038-44.

[4]. Xu Z, et al.Mitochondrial fusion/fission process involved in the improvement of catalpol on high glucose-induced hepatic mitochondrial dysfunction. Acta Biochim Biophys Sin (Shanghai). 2015 Jul 2.

 Chemical & Physical Properties

Density 1.7±0.1 g/cm3
Boiling Point 675.6±55.0 °C at 760 mmHg
Melting Point 203-205ºC
Molecular Formula C15H22O10
Molecular Weight 362.329
Flash Point 362.4±31.5 °C
Exact Mass 362.121307
PSA 161.60000
LogP -4.15
Vapour Pressure 0.0±4.7 mmHg at 25°C
Index of Refraction 1.679
Storage condition ?20°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LZ5776816
CHEMICAL NAME :
beta-D-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-hydroxy- 1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran- 2-yl, (1aS-(1a-alpha,1b-beta,2-beta,5a- beta,6-beta,6a-alpha))-
CAS REGISTRY NUMBER :
2415-24-9
LAST UPDATED :
199806
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C15-H22-O10

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 64,93,1968
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 64,93,1968

 Safety Information

Hazard Codes Xi: Irritant;
Risk Phrases R36/37/38
Safety Phrases S26
RIDADR NONH for all modes of transport
RTECS LZ5776816

 Synthetic Route

rehmannioside B structure

rehmannioside B

CAS#:81720-06-1

~%

Catalpol Structure

Catalpol

CAS#:2415-24-9

Literature: Oshio,H.; Inouye,H. Phytochemistry (Elsevier), 1982 , vol. 21, p. 133
2',3',4',6,6',10-Hexaacetylcatalpol structure

2',3',4',6,6',1...

CAS#:6910-20-9

~%

(8S)-(-)-7,8-Dihydro-8-hydroxyaucubin structure

(8S)-(-)-7,8-Di...

CAS#:81892-75-3

Catalpol Structure

Catalpol

CAS#:2415-24-9

Literature: Phytochemistry (Elsevier), , vol. 21, p. 231
2',3',4',6',10-Pentaacetyl-6-(4-acetylvanilloyl)catalpol structure

2',3',4',6',10-...

CAS#:75598-56-0

~%

Vanillic acid structure

Vanillic acid

CAS#:121-34-6

Catalpol Structure

Catalpol

CAS#:2415-24-9

Literature: Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, , vol. 43, # 5 p. 1023 - 1025
[(1aS,1bS,2S,5aR,6S,6aS)-2-(β-D-glucopyranosyloxy)-1b,5a,6,6a-tetrahydro-6-methoxyoxireno[4,5]cyclopenta[1,2-c]pyran-1a(2H)-yl]methyl 3,4-dimethoxybenzoate structure

[(1aS,1bS,2S,5a...

CAS#:1374308-81-2

~%

Veratric acid structure

Veratric acid

CAS#:93-07-2

Catalpol Structure

Catalpol

CAS#:2415-24-9

Literature: Helvetica Chimica Acta, , vol. 95, # 4 p. 586 - 593

 Articles26

More Articles
HPLC-APCI-MS/MS method for the determination of catalpol in rat plasma and cerebrospinal fluid: application to an in vivo pharmacokinetic study.

J. Pharm. Biomed. Anal. 70 , 337-43, (2012)

Catalpol is a Chinese herb ingredient with potential for the treatment of neurodegenerative disorders. A high-performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spe...

[Simultaneous determination and optimization of extraction process of catalpol and acteoside from rehmanniae radix].

Zhong Yao Cai 35(8) , 1318-22, (2012)

To establish a method for simultaneously quantification of the Catalpol and Acteoside from Rehmanniae Radix and optimize the extraction process from Rehmanniae Radix by response surface methodology (R...

Synergistic effects of iridoid glycosides on the survival, development and immune response of a specialist caterpillar, Junonia coenia (Nymphalidae).

J. Chem. Ecol. 38(10) , 1276-84, (2012)

Plants use a diverse mix of defenses against herbivores, including multiple secondary metabolites, which may affect herbivores synergistically. Chemical defenses also can affect natural enemies of her...

 Synonyms

EINECS 219-324-0
catalpinoside
des-p-hydroxybenzoyl-catalposid
CATAPOL
6-Hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-2-yl hexopyranoside
Hexopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl
catalposide
methyl iridoid glycoside
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