CAS 315-22-0: Monocrotaline

Description: Monocrotaline is a naturally occurring alkaloid primarily derived from the plant species *Crotalaria* and is known for its toxic properties. It belongs to the class of pyrrolizidine alkaloids, which are characterized by a bicyclic structure containing a pyrrolizidine ring. Monocrotaline exhibits hepatotoxicity and can cause pulmonary hypertension, making it a subject of interest in toxicology and pharmacology. The compound is known to undergo metabolic activation in the liver, leading to the formation of reactive metabolites that can damage cellular structures, particularly in the liver and lungs. Its mechanism of action involves the formation of DNA adducts, which can result in mutagenic effects. Due to its toxic nature, monocrotaline is often studied in the context of environmental health and safety, particularly regarding exposure risks associated with certain plants. Additionally, it has been used in research to model pulmonary hypertension in animal studies, providing insights into the disease mechanisms and potential therapeutic approaches.

Formula: C₁₆H₂₃NO₆

InChI: InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1

InChI key: InChIKey=QVCMHGGNRFRMAD-XFGHUUIASA-N

SMILES: O=C1OC2CCN3CC=C(COC(=O)C(O)(C)C(O)(C)C1C)C32

Synonyms:

• (13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
• (2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-
• (3R,4R,5R,13aR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
• (3R,4R,5R,13aR,13bR)-4,5,8,10,12,13,13a,13b-Octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
• (3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-2,6-dioxo-3,4,5,6,8,10,12,13,13a,13b-decahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizin-11-ium
• (3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
• (3R,4R,5R,13aR,13bS)-4,5-dihydroxy-3,4,5-trimethyl-2,6-dioxo-3,4,5,6,8,10,12,13,13a,13b-decahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizin-11-ium
• (3R,4S,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
• (3S,4S,5S,13aS,13bS)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
• 12-beta,13-beta-Dihydroxy-12-alpha,13-alpha,14-alpha-trimethylcrotal-1-enine
• 14,19-Dihydro-12,13-dihydroxy(13-alpha,14-alpha)-20-norcrotalanan-11,15-dione
• 14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
• 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-
• 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)- (9CI)
• 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13alpha,14alpha)-
• 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13α,14α)-
• 2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-
• 2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine, 20-norcrotalanan-11,15-dione deriv.
• 2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, [3R-(3R*,4R*,5R*,13aR*,13bR*)]-
• A 6080
• Brn 0048732
• Ccris 416
• Crotaline
• Hsdb 3513
• Monocrotalin
• Nci-C56462
• Nsc 28693
• Retronecine cyclic 2,3-dihydroxy-2,3,4-trimethylglutarate
• Monocrotaline
• 4-27-00-06660 (Beilstein Handbook Reference)

Monocrotalin

CAS: 315-22-0

Monocrotalin analytical standard provided with chromatographic purity, to be used as reference material for qualitative …

• Formula: C₁₆H₂₃NO₆
• Purity: (HPLC) ≥90%
• Color and Shape: Powder
• Molecular weight: 325.37

MONOCROTALINE

CAS: 315-22-0

• Formula: C₁₆H₂₃NO₆
• Purity: 95%
• Color and Shape: Solid
• Molecular weight: 325.3569

Monocrotaline (Crotaline)

CAS: 315-22-0

• Formula: C₁₆H₂₃NO₆
• Molecular weight: 325.36

(3R,4R,5R,8A1R,13Ar)-4,5-Dihydroxy-3,4,5-Trimethyl-4,5,8,8A1,10,12,13,13A-Octahydro-2H-[1,6]Dioxacycloundecino[2,3,4-Gh]Pyrrolizine-2,6(3H)-Dione

CAS: 315-22-0

• Purity: 98%
• Molecular weight: 325.36g/mol

Monocrotaline

CAS: 315-22-0

• Formula: C₁₆H₂₃NO₆
• Purity: 99%
• Molecular weight: 325.361

Monocrotaline

CAS: 315-22-0

• Formula: C₁₆H₂₃NO₆
• Color and Shape: Neat
• Molecular weight: 325.36

Crotaline

CAS: 315-22-0

• Formula: C₁₆H₂₃NO₆
• Purity: ≥ 98.0%
• Color and Shape: White to off-white crystalline powder
• Molecular weight: 325.36

Monocrotaline-d3

CAS: 315-22-0

• Formula: C₁₆H₂₀D₃NO₆
• Molecular weight: 328.38

Monocrotaline

CAS: 315-22-0

Monocrotaline (Crotaline) is a pyrrolizidine alkaloid and has certain cellular activity against HepG2 cells.Cost-effective and …

• Formula: C₁₆H₂₃NO₆
• Purity: 98% - 99.94%
• Color and Shape: White To Light Tan Powder
• Molecular weight: 325.36

Monocrotaline

CAS: 315-22-0

Natural alkaloid

• Formula: C₁₆H₂₃NO₆
• Purity: ≥ 95.0 % (HPLC)
• Color and Shape: Powder
• Molecular weight: 325.36

Monocrotaline

CAS: 315-22-0

Applications A toxic pyrrolizidine alkaloid isolated from Crotalaria spp. It is used for inducing pulmonary …

• Formula: C₁₆H₂₃NO₆
• Color and Shape: White To Off-White
• Molecular weight: 325.36

Monocrotaline

CAS: 315-22-0

• Purity: 99.0%
• Color and Shape: Solid
• Molecular weight: 325.3609924316406

Monocrotaline

CAS: 315-22-0

Toxin; induces pulmonary hypertension

• Formula: C₁₆H₂₃NO₆
• Purity: Min. 98%
• Color and Shape: White Off-White Clear Liquid
• Molecular weight: 325.36 g/mol

Monocrotaline-d4

CAS: 315-22-0

Applications Monocrotaline-d4 is labelled Monocrotaline (M526000) which is a toxic pyrrolizidine alkaloid isolated from Crotalaria …

• Formula: C₁₆D₄H₁₉NO₆
• Color and Shape: Neat
• Molecular weight: 329.382