NISTC15503874 Chemical Properties

Melting point:

178-180℃

Boiling point:

583.2±50.0 °C(Predicted)

Density 

1.32±0.1 g/cm3 (20 ºC 760 Torr)

solubility 

DMF: insol; DMSO: 1 mg/ml; Ethanol: insol; PBS (pH 7.2): 5 mg/ml

form 

A solid

pka

12.00±0.40(Predicted)

color 

White to off-white

InChI

InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1

InChIKey

BCJMNZRQJAVDLD-FXGRWVCYSA-N

SMILES

N12CC=C3COC(=O)[C@@](O)(CO)[C@H](C)C/C(=C\C)/C(=O)O[C@@]([H])([C@]13[H])CC2

CAS DataBase Reference

15503-87-4

NISTC15503874 Usage And Synthesis

Description

A pyrrolizidine alkaloid first isolated from Crotalaria usararnoensis E. G. Baker, this base has more recently been found in C. brevifolia and C. rnucronata. The alkaloid has [α]²⁰_D + 6.1° (c 0.38, EtOH) or + 7.1° (c 1.83, EtOH). It yields a picrate, m.p. 230- 2°C (dec.); picrolonate, m.p. 148-150°C (dec.); reineckate, m.p. 190-2°C (dec.) and methiodide, m.p. 229-230°C (dec.). Alkaline hydrolysis furnishes retronecine and retronecic acid, m.p. 177-9°C. It has been suggested that the base may be identical with Mucronatine (q.v.).

Uses

Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50% of biofilm formation without killing the bacteria[1].

Definition

ChEBI: LSM-2938 is a macrolide.

Hazard

A poison.

References

Culvenor, Smith., Austral. J. Chern., 19,2127 (1966)
Sawhney et al., Ind. J. Chern., 5, 655 (1967)

NISTC15503874(15503-87-4)Related Product Information

• Cevadine
• veratramine
• Usaramine N-oxide
• daurisoline
• VERATRIDINE
• L-Hyoscyamine
• Xanthiazone
• menisdaurin
• (13R,14R)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione 4-oxide
• Xanthiside
• 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one
• Daurinoline
• MONOCROTALINE