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522-17-8

Basic Information
CAS No.: 522-17-8
Name: DEGUELIN
Article Data: 16
Molecular Structure:
Molecular Structure of 522-17-8 (DEGUELIN)
Formula: C23H22O6
Molecular Weight: 394.424
Synonyms: 3H-Bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one,13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl- (7CI,8CI);3H-Bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one,13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)- (9CI);3H-Bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-,(7aS-cis)-;Deguelin (6CI);(-)-cis-Deguelin;
EINECS: 200-258-5
Density: 1.255 g/cm3
Melting Point: 85-87 °C(lit.)
Boiling Point: 560.127 °C at 760 mmHg
Flash Point: 244.739 °C
Safety: 22-24/25
PSA: 63.22000
LogP: 4.00790
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Specification

The (-)-Deguelin, with the CAS registry number 522-17-8, is also known as 3H-Bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-,(7aS-cis)-. It belongs to the product categories of Miscellaneous Natural Products; Antitumour. This chemical's molecular formula is C23H22O6 and molecular weight is 394.42. What's more, its systematic name is (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one. You should not breathe dust. When using it, you must avoid contact with skin and eyes. This chemical is a derivative of rotenone. Both are compounds classified as rotenoids of the flavonoid family and are naturally occurring insecticides. They can be produced by extraction from several plant species belonging to three genera of the Fabaceae or Legume family, Lonchocarpus, Derris, or Tephrosia. This substance should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides, heat and fire.

Physical properties of (-)-Deguelin are: (1)ACD/LogP: 4.423; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.42; (4)ACD/LogD (pH 7.4): 4.42; (5)ACD/BCF (pH 5.5): 1354.31; (6)ACD/BCF (pH 7.4): 1354.31; (7)ACD/KOC (pH 5.5): 6071.30; (8)ACD/KOC (pH 7.4): 6071.30; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 63.22 Å2; (13)Index of Refraction: 1.584; (14)Molar Refractivity: 105.086 cm3; (15)Molar Volume: 314.213 cm3; (16)Polarizability: 41.659×10-24cm3; (17)Surface Tension: 43.2 dyne/cm; (18)Density: 1.255 g/cm3; (19)Flash Point: 244.739 °C; (20)Enthalpy of Vaporization: 84.263 kJ/mol; (21)Boiling Point: 560.127 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2c5c(O[C@@H]3COc1cc(OC)c(OC)cc1[C@H]23)c4\C=C/C(Oc4cc5)(C)C
(2)Std. InChI: InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
(3)Std. InChIKey: ORDAZKGHSNRHTD-UXHICEINSA-N

The toxicity data is as follows

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo oral 1gm/kg (1000mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Industrial and Engineering Chemistry. Vol. 29, Pg. 429, 1937.
rabbit LD oral > 1500mg/kg (1500mg/kg)   Industrial and Engineering Chemistry. Vol. 29, Pg. 429, 1937.
rat LD oral > 2gm/kg (2000mg/kg)   Industrial and Engineering Chemistry. Vol. 29, Pg. 429, 1937.