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CAS

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10285-07-1

LYCOPSAMINE is a primary reference substance with assigned absolute purity, which is an amorphous pyrrolizidine alkaloid isolated from various plant sources such as Arnsinckia hispida, A. intermedia, and A. lycopsoides. It is dextrorotatory and has alkaline hydrolysis properties, yielding retronecine and viridifloric acid.

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  • 10285-07-1 Structure

  • Basic information

    1. Product Name: LYCOPSAMINE
    2. Synonyms: LYCOPSAMINE;(2S,3S)-2,3-Dihydroxy-2-isopropylbutanoic acid [(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizine-7-yl]methyl ester;(2S,3S)-2,3-Dihydroxy-2-isopropylbutanoic acid [(7R)-7β-hydroxy-5,6,7,7aα-tetrahydro-3H-pyrrolizine-1-yl]methyl ester;(1R-(1alpha,7(2S*,3S*),7Abeta))-(2,3,5,7A-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl 2,3-dihydroxy-2-(1-methylethyl)butanoate;Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, ((1R,7ar)-2,3,5,7A-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (2S,3S)-;Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7A-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (1R-(1alpha,7(2S*,3S*),7abeta))-;Ccirs 9199;Ccris 9199
    3. CAS NO:10285-07-1
    4. Molecular Formula: C15H25NO5
    5. Molecular Weight: 299.36
    6. EINECS: N/A
    7. Product Categories: Amines, Heterocycles
    8. Mol File: 10285-07-1.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 463.3°Cat760mmHg
    3. Flash Point: 234°C
    4. Appearance: /
    5. Density: 1.26±0.1 g/cm3 (20 ºC 760 Torr)
    6. Vapor Pressure: 1.57E-10mmHg at 25°C
    7. Refractive Index: 1.567
    8. Storage Temp.: -20°C
    9. Solubility: Chloroform, Ethanol
    10. CAS DataBase Reference: LYCOPSAMINE(CAS DataBase Reference)
    11. NIST Chemistry Reference: LYCOPSAMINE(10285-07-1)
    12. EPA Substance Registry System: LYCOPSAMINE(10285-07-1)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. RIDADR: 1544
    5. WGK Germany:
    6. RTECS:
    7. HazardClass: 6.1(b)
    8. PackingGroup: III
    9. Hazardous Substances Data: 10285-07-1(Hazardous Substances Data)

10285-07-1 Usage

Uses

Used in Toxicological Research:
LYCOPSAMINE is used as a hepatotoxin and tumorigen for studying the effects of pyrrolizidine alkaloid-containing plants on livestock, wildlife, and humans. It helps in understanding the biological biomarker of pyrrolizidine alkaloid-induced liver tumor formation through pyrrolizidine Alkaloid-Derived DNA Adducts.

References

Cu1venor, Smith., Austral. 1. Chern., 19, 1955 (1966)

Check Digit Verification of cas no

The CAS Registry Mumber 10285-07-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,2,8 and 5 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 10285-07:
(7*1)+(6*0)+(5*2)+(4*8)+(3*5)+(2*0)+(1*7)=71
71 % 10 = 1
So 10285-07-1 is a valid CAS Registry Number.
InChI:InChI=1/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12+,13+,15-/m0/s1

10285-07-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate

1.2 Other means of identification

Product number -
Other names retronecine-O(9)-(-)-viridifloryl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10285-07-1 SDS

10285-07-1Downstream Products

10285-07-1Relevant articles and documents

Ideamine N-Oxides: Pyrrolizidine Alkaloids Sequestered by the Danaine Butterfly, Idea leuconoe

Nishida, Ritsuo,Kim, Chul-Sa,Fukami, Hiroshi,Irie, Ryozo

, p. 1787 - 1792 (2007/10/02)

Two new pyrrolizidine alkaloids, ideamines A and B, together with other analogs (lycopsamine and parsonsine) were isolated in the N-oxide forms from adult bodies of the Apocynaceae-feeding danaine butterfly, Idea leuconoe.Ideamine A was characterized as a homolog of lycopsamine, in which the viridifloric acid moiety was replaced by a 2-ethyl-2,3-dihydroxybutanoic moiety.Likewise, ideamine B was identified as a nor-derivative of parsonsine, in which the trachelanthic acid moiety was replaced by a 2-ethyl-2,3-dihydroxybutanoic moiety diastereomeric to the necic acid from ideamine A.

Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents

Zalkow,Glinski,Gelbaum,Fleischmann,McGowan,Gordon

, p. 687 - 694 (2007/10/02)

(-)- and (+)-trachelanthic and (-)- and (+)-viridifloric acids were synthesized and their isopropylidene derivatives were regiospecifically coupled, at C-9, with (-)-retronecine (2) obtained by hydrolysis of monocrotaline (1), isolated from Crotalaria spectabilis. Hydrolysis, followed by oxidation, led to the N-oxides of indicine (7), intermedine (13), lycopsamine (15), and the new nonnatural product 16, respectively. Each of these analogues was screened in the P388 lymphocytic leukemia system at the same time as indicine N-oxide, and the results were compared. Other related analogues were prepared and similarly screened and the results compared with those from indicine N-oxide.

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