Deguelin

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Names

[ CAS No. ]:
522-17-8

[ Name ]:
Deguelin

[Synonym ]:
3H-[1]Benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)-
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)-
UNII-K5Z93K66IE
Deguelin
Tocris-1770
(7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one
MFCD01740600
(-)-cis-Deguelin
(7aS-cis)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one
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)-

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
560.1±50.0 °C at 760 mmHg

[ Melting Point ]:
85-87ºC(lit.)

[ Molecular Formula ]:
C23H22O6

[ Molecular Weight ]:
394.417

[ Flash Point ]:
244.7±30.2 °C

[ Exact Mass ]:
394.141632

[ PSA ]:
63.22000

[ LogP ]:
5.03

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.584

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DX1500000
CAS REGISTRY NUMBER :
522-17-8
LAST UPDATED :
199406
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C23-H22-O6

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IECHAD Industrial and Engineering Chemistry. (Washington, DC) V.15-62, 1923-70. For publisher information, see CHMTBL. Volume(issue)/page/year: 29,429,1937
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>1500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IECHAD Industrial and Engineering Chemistry. (Washington, DC) V.15-62, 1923-70. For publisher information, see CHMTBL. Volume(issue)/page/year: 29,429,1937
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
IECHAD Industrial and Engineering Chemistry. (Washington, DC) V.15-62, 1923-70. For publisher information, see CHMTBL. Volume(issue)/page/year: 29,429,1937

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DX1500000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • Rotenonic acid
  • Tephrosin
  • amorphispironone
  • (6aS,12S,12aS,5'S)-12-deoxo-12-hydroxy-5'-phenylthio-4',5'-dihydrodeguelin
  • Rotenone
  • (6aS,12aS)-8-(4-bromo-3-methylbut-2-en-1-yl)-9-hydroxy-2,3-dimethoxy-6,6a-dihydrochromeno[3,4-b]chromen-12(12aH)-one
  • diazomethane

DownStream

  • Dehydrodeguelin
  • 5-hydroxy-2,2-dimethylchromene-6-carboxylic acid

Articles

Concise modular asymmetric synthesis of deguelin, tephrosin and investigation into their mode of action.

Chemistry 16(32) , 9767-71, (2010)

In vitro approach to predict post-translational phosphorylation response to mixtures.

Toxicology 313(2-3) , 113-21, (2013)

While exposure to chemical mixtures is an everyday reality, an understanding of their combined effects, and any potential prediction thereof, is extremely limited. Realistic exposures potentially cons...

Exploring the boundaries of additivity: mixtures of NADH: quinone oxidoreductase inhibitors.

Chem. Res. Toxicol. 24(8) , 1242-50, (2011)

The activity of mitochondrial complex I of the electron transport chain (ETC) is known to be affected by an extraordinarily large number of diverse xenobiotics, and dysfunction at complex I has been a...


More Articles

Related Compounds

  • deguelin
  • (S)-3-Amino-2-methylpropan-1-OL hydrochloride
  • Sodium;4-[3-(3-fluorophenyl)-5,5-dimethyl-4-oxofuran-2-yl]benzenesulfinate
  • 2-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoxazole
  • B-[9,9-Dimethyl-7-(10-phenyl-9-anthracenyl)-9H-fluoren-2-yl]boronic acid
  • (R,E)-(3-((tert-Butoxycarbonyl)amino)but-1-en-1-yl)boronic acid
  • 4-(7-Azidoheptylamino)-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione
  • N-[4-Chloro-3-(methoxymethyl)phenyl]prop-2-enamide
  • Benzyl (aminomethyl)carbamate trifluoroacetate
  • (R)-7-Fluoro-5-oxa-2-azaspiro[3.5]nonane hydrochloride
  • 7-Fluoro-5-oxa-2-azaspiro[3.5]nonane hydrochloride
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