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=1/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/p+1/t9-,11+,12+,15+,16-/m0/s1

InChI key: InChIKey=QVCMHGGNRFRMAD-XFGHUUIASA-N

SMILES: O=C1O[C@]2([C@@]3(N(CC2)CC=C3COC(=O)[C@](C)(O)[C@](C)(O)[C@H]1C)[H])[H]

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)
• 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
• MONOCROTOLLINE (99%)
• Bulbus Lilii
• Monocrotoline
• CROTALIN
• (13-alpha,14-alpha)-14,19-dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dio
• Monocrotaline/crotaline
• Monocrotaline, >=98%
• MONOCRATALINE
• Monccrotalire
• (2,3,4-gh)pyrrolizine-2,6(3h)-dione,(4,5,8,10,12,13,1
• Monocrotalinum
• 14,19-Dihydro-12,13-dihydroxy(13alpha,14alpha)-20-norcrotalanan-11,15-dione
• MONOCROTALIN(CROTALIN)(RG)
• 5-trimethyl-2h-(1,6)dioxacycloundecino-droxy-4
• 20-norcrotalanan-11,15-dione,14,19-dihydro-12,13-dihydroxy-,(13-alpha,14-al
• (2,3,4-gh)pyrrolizine-2,6(3h)-dione,(4,5,8,10,12,13,13a,13b-octahydro-4,5-dihy
• Crotaline,Monocrotaline
• Monocrotaline,99%
• (13R,14R)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione

Monocrotalin

CAS: 315-22-0

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

Formula: C₁₆H₂₃NO₆

Purity: (HPLC) ≥90%

Color and Shape: Powder

Molecular weight: 325.37

Ref: 11-7351

Monocrotaline

CAS: 315-22-0

Formula: C₁₆H₂₃NO₆

Purity: 95%

Color and Shape: Solid

Molecular weight: 325.3569

Ref: IN-DA00BYAV

(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

(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

Purity: 98%

Molecular weight: 325.36g/mol

Ref: 54-OR1026386

Monocrotaline (Crotaline)

CAS: 315-22-0

Formula: C₁₆H₂₃NO₆

Molecular weight: 325.36

Ref: 4Z-M-167001

Monocrotaline

CAS: 315-22-0

Monocrotaline

Purity: ≥95%

Molecular weight: 325.36g/mol

Ref: 54-BUP15752

Crotaline

CAS: 315-22-0

Formula: C₁₆H₂₃NO₆

Purity: ≥ 98.0%

Color and Shape: White to off-white crystalline powder

Molecular weight: 325.36

Ref: 7W-GX1396

Monocrotaline

CAS: 315-22-0

Formula: C₁₆H₂₃NO₆

Purity: 99%

Molecular weight: 325.361

Ref: BP-BP0957

Monocrotaline

Controlled Product

CAS: 315-22-0

Formula: C₁₆H₂₃NO₆

Color and Shape: Neat

Molecular weight: 325.36

Ref: 04-C15298000

Monocrotaline-d3

CAS: 315-22-0

Formula: C₁₆H₂₀D₃NO₆

Molecular weight: 328.38

Ref: 4Z-M-167003

Monocrotaline

CAS: 315-22-0

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

Formula: C₁₆H₂₃NO₆

Purity: 98% - 99.94%

Color and Shape: White To Light Tan Powder

Molecular weight: 325.36

Ref: TM-T2803

Monocrotaline

CAS: 315-22-0

Natural alkaloid

Formula: C₁₆H₂₃NO₆

Purity: ≥ 95.0 % (HPLC)

Color and Shape: Powder

Molecular weight: 325.36

Ref: 5G-89251

Monocrotaline

CAS: 315-22-0

Applications A toxic pyrrolizidine alkaloid isolated from Crotalaria spp. It is used for inducing pulmonary diseases in rats.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Newberne, P.M., et al.: Toxicol. Appl. Pharmacol., 18, 387 (1971), Bober, M.A., et al.: Toxicon, 27, 1059 (1989), Wilson, D.W., et al.: Crit. Rev. Toxicol., 22, 307 (1992),

Formula: C₁₆H₂₃NO₆

Color and Shape: White To Off-White

Molecular weight: 325.36

Ref: TR-M526000

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

Ref: 3D-FM64904

Monocrotaline

CAS: 315-22-0

Formula: C₁₆H₂₃NO₆

Purity: 99.0%

Color and Shape: Solid

Molecular weight: 325.361

Ref: 10-F002602

Monocrotaline-d4

Controlled Product

CAS: 315-22-0

Applications Monocrotaline-d4 is labelled Monocrotaline (M526000) which is a toxic pyrrolizidine alkaloid isolated from Crotalaria spp. It is used for inducing pulmonary diseases in rats.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Newberne, P.M., et al.: Toxicol. Appl. Pharmacol., 18, 387 (1971), Bober, M.A., et al.: Toxicon, 27, 1059 (1989), Wilson, D.W., et al.: Crit. Rev. Toxicol., 22, 307 (1992),

Formula: C₁₆D₄H₁₉NO₆

Color and Shape: Neat

Molecular weight: 329.382

Ref: TR-M526002