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2415-24-9

Basic Information
CAS No.: 2415-24-9
Name: Catalpol
Molecular Structure:
Molecular Structure of 2415-24-9 (Catalpol)
Formula: C15H22O10
Molecular Weight: 362.33
Synonyms: Catalpol(7CI,8CI);b-D-Glucopyranoside,1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl,[1aS-(1aa,1bb,2b,5ab,6b,6aa)]-;Catalpinoside;De(p-hydroxybenzoyl)catalposide;
EINECS: 219-324-0
Density: 1.72 g/cm3
Melting Point: 203-205 °C
Boiling Point: 675.6 °C at 760 mmHg
Flash Point: 362.4 °C
Solubility:
Appearance: powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information:
PSA: 161.60000
LogP: -3.59030
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Chemistry

Product Name: Catalpol
Molecular Structure of Catalpol (CAS NO.2415-24-9):

Molecular Formula: C15H22O10
Molecular Weight: 362.3292
Synonyms of Catalpol (CAS NO.2415-24-9): Catalpinoside ; Catalposide, des-p-hydroxybenzoyl- ; De(p-hydroxybenzoyl)catalposide ; EINECS 219-324-0 ; (1AS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl-beta-D-glucopyranoside ; 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))- ; 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-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-
CAS NO: 2415-24-9
Product Categories: Iridoids
Melting point: 203-205°C 
Polar Surface Area: 95.6 Å2
Index of Refraction: 1.679
Molar Refractivity: 79.2 cm3
Molar Volume: 209.7 cm3
Surface Tension: 97.9 dyne/cm
Density of Catalpol (CAS NO.2415-24-9): 1.72 g/cm3
Flash Point: 362.4 °C
Enthalpy of Vaporization: 113.49 kJ/mol
Boiling Point: 675.6 °C at 760 mmHg
Vapour Pressure: 3.77E-21 mmHg at 25°C

Uses

Primary function of Catalpol (CAS NO.2415-24-9) is to stimulate the production of adrenal cortical hormones, it is increases the production of sex hormones. Catalpol also exhibits anti-inflammatory activity and has shown to increase the production of androgens yielded by the adrenal gland, it can lead to increases in muscle mass.

Production

 Catalpol (CAS NO.2415-24-9) can synthesis by biosynthetic pathway. At frist, extract from geraniol with epi-iridodial. Addition of a glucose at carbon 1 (C1) of the iridoid backbone and oxidation of the aldehyde at C4 of epi-iridotrial produced 8-epiloganic acid. A subquent hydrolysis at C8 yielded mussaenosidic acid, followed by a dehydration to yield deoxyngeniposidic acid. The next precursor, geniposidic acid, was furnished via hydrolysis of C10, and then a decarboxylation to remove the carboxylic acid at C4 provided bartsioside. The very widely known and accepted precursor to catalpol, aucubin, was then furnished via hydroxylation at C6. Finally an epoxidation with the alcohol at C10 yielded the natural product, catalpol.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intravenous > 2500mg/kg (2500mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 93, 1968.
mouse LD oral > 10gm/kg (10000mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 93, 1968.

Safety Profile

Hazard Codes of Catalpol (CAS NO.2415-24-9): IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.