(15E)-12,18-Dihydroxysenecionan-11,16-dione

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Names

[ CAS No. ]:
15503-87-4

[ Name ]:
(15E)-12,18-Dihydroxysenecionan-11,16-dione

[Synonym ]:
trans-Retrorsin
C18H25NO6
(15E)-12,18-dihydroxy-senecionane-11,16-dione
[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, (3E,5R,6S,14aR,14bR)-
Senecionan-11,16-dione,12,18-dihydroxy-,(15E)
trans-Retrorsine
(15E)-Retrorsine
(15E)-12,18-Dihydroxysenecionan-11,16-dione
Mucronatine
Usaramin
(+)-Ursamine
Mucronatine (7CI)

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
583.2±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C18H25NO6

[ Molecular Weight ]:
351.394

[ Flash Point ]:
306.5±30.1 °C

[ Exact Mass ]:
351.168182

[ PSA ]:
96.30000

[ LogP ]:
-0.14

[ Vapour Pressure ]:
0.0±3.7 mmHg at 25°C

[ Index of Refraction ]:
1.590

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VT5707200
CHEMICAL NAME :
Senecionan-11,16-dione, 12,18-dihydroxy-, (15E)-
CAS REGISTRY NUMBER :
15503-87-4
LAST UPDATED :
199012
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C18-H25-N-O6
MOLECULAR WEIGHT :
351.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
35 mg/kg
TOXIC EFFECTS :
Liver - other changes
REFERENCE :
CBINA8 Chemico-Biological Interactions. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1969- Volume(issue)/page/year: 12,299,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 7,144,1969

Synthetic Route

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Precursor & DownStream

Precursor

  • (+)-Citronellal
  • (R)-Citronellol
  • (R)-(+)-CITRONELLIC ACID
  • (3R)-α-methylene-3,7-dimethyl-6-octen-1-al
  • (4R)-2,2-Dimethyl-4-[1(1R)-1,5-dimethyl-4-hexenyl]-4-(hydroxymethyl)-1,3-dioxolane
  • (2S,3R)-3,7-Dimethyl-2-hydroxy-2-(hydroxymethyl)-6-octenyl Pivalate
  • (4R,5S)-5-[[2-(Trimethylsilyl)ethoxy]carbonyl]-5-(hydroxymethyl)-4-methyl-5-pentanolide
  • (4S)-2,2-Dimethyl-4-[1(1R)-1,5-dimethyl-4-hexenyl]-4-[(pivalyloxy)methyl]-1,3-dioxolane
  • (4R,5S,E)-2-ethylidene-5-hydroxy-5-(hydroxymethyl)-4-methyl-6-oxo-6-(2-(trimethylsilyl)ethoxy)hexanoic acid
  • (2S,3R,E)-2-(trimethylsilyl)ethyl 5-ethylidene-2-(hydroxymethyl)-3-methyl-6-oxotetrahydro-2H-pyran-2-carboxylate

DownStream

Related Compounds

  • isatidine
  • Riddelline
  • dehydroretrorsine
  • 12,18-Dihydroxysenecionan-11,16-dione hydrochloride
  • 4H-1,13-Methano[1,7]dioxacyclotridecino[4,3-b]pyrrole-6,11-dione,10-ethylidene-2,7,8,9,10,13,14,14a-octahydro-7,14-dihydroxy-7,8-dimethyl-,(7R,8R,10E,13S,14R,14aR)- (9CI)
  • Neoplatyphylline
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1,3-Dimethoxy-4-[(E)-1,3-diphenylallyl]benzene
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • 2-(1-ethyl-1H-pyrazol-4-yl)-2-methoxyethan-1-amine
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine