548-42-5

Basic information

• Product Name: AGROCLAVINE
• Synonyms: 8,9-didehydro-6,8-dimethylergoline;AGROCLAVINE;ERGOLINE,8,9-DIDEHYDRO-6,8-DIMETHYL-;Agroclavin;NSC 93132;8,9-didehydro-6,8-dimethyl-ergolin
• CAS NO: 548-42-5
• Molecular Formula: C₁₆H₁₈N₂
• Molecular Weight: 238.33
• EINECS: 208-947-3
• Mol File: 548-42-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 198-208℃ (decomposition) (ethyl ether )
• Boiling Point: 370.93°C (rough estimate)
• Flash Point: 209.3°C
• Appearance: /
• Density: 0.9597 (rough estimate)
• Vapor Pressure: 2.4E-07mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 17.49±0.40(Predicted)
• CAS DataBase Reference: AGROCLAVINE(CAS DataBase Reference)
• NIST Chemistry Reference: AGROCLAVINE(548-42-5)
• EPA Substance Registry System: AGROCLAVINE(548-42-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• Hazardous Substances Data: 548-42-5(Hazardous Substances Data)

Usage

Uses

Agroclavine is an ergot alkaloid and a fungal metabolite. It is also an environmental and food contaminant.

Definition

ChEBI: An ergot alkaloid that is ergoline which contains a double bond between positions 8 and 9, and which is substituted by methyl groups at positions 6 and 8.

Purification Methods

It crystallises from diethyl ether or Me2CO. The hydrochloride crystallises from H2O and has m 265-266o, [] 20 -110o (CHCl3). [Plieninger et al. Justus Liebigs Ann Chem 743 95 1971,Beilstein 23 III/IV 1623.]

InChI:InChI=1/C16H18N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,13,15,17H,7,9H2,1-2H3

Upstream product

• 548-43-6 elymoclavine 
• 73-22-3 L-Tryptophan 
• 478-91-1 Lysergen 
• 120408-46-0 HCl salt of N-p-Ts lysergene 
• 1150-44-3 Isochanoclavin-(I) 
• 68156-97-8 (4R,5R)-N-methyl-5-(2-methylprop-1-en-1-yl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine 
• 25800-42-4 (E)-2-methyl-3-((4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)acrylaldehyde 
• 487-89-8 Indole-3-carboxaldehyde 
• 115698-38-9 (E)-methyl 3-(3-formyl-1H-indol-4-yl)acrylate 
• 99499-50-0 (3β,8α,9α)-2,3-Dihydro-8-methanesulfonyloxymethyl-1-<(4-methoxyphenyl)sulfonyl>-6-methylergolin-9-ol 
• 89651-07-0 (3aβ,5aα,6aα,11bα,11cβ)-5,5a,6,6a,7,8,11b,11c-Octahydro-8-<(4-methoxyphenyl)sulfonyl>-5-methylfuro<4,3-fg>quinolin-4(3aH)-one 
• 89651-07-0 (3aβ,5aβ,6aβ,11bα,11cβ)-5,5a,6,6a,7,8,11b,11c-Octahydro-8-<(4-methoxyphenyl)sulfonyl>-5-methylfuro<4,3-fg>quinolin-4(3aH)-one 
• 101926-52-7 (3β,8α,9β)-8,9-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6,8-dimethylergoline 

Downstream Products

• 89930-59-6 1-propyl-agroclavine 
• 123630-15-9 8-phenylthiolysergine 
• 1935-33-7 1-methyl-agroclavine 
• 548-43-6 elymoclavine 
• 34263-09-7 6-Nor-agroclavin 
• 189179-68-8 C₃₇H₃₈N₂O₅ 
• 189179-65-5 C₃₇H₃₈N₂O₅ 
• 519-12-0 (+)-setoclavine 
• 478-89-7 Pyroclavin 
• 569-26-6 festuclavine 
• 436-41-9 (+)-Costaclavine 

Relevant articles and documents

Regioselective Direct C-4 Functionalization of Indole: Total Syntheses of (-)-Agroclavine and (-)-Elymoclavine

An efficient rhodium-catalyzed method for direct C-H functionalization at the C4 position of unprotected indoles has been developed. The utility of this method is demonstrated by the concise total syntheses of agroclavine and elymoclavine in a divergent manner. These syntheses feature a Pd-catalyzed asymmetric allylic alkylation reaction to assemble the triyclic indole moiety, and a ring-closing metathesis reaction to form the D ring.

New insights into ergot alkaloid biosynthesis in Claviceps purpurea: An agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine

Ergot alkaloids are indole derivatives with diverse structures and biological activities. They are produced by a wide range of fungi with Claviceps purpurea as the most important producer for medical use. Chanoclavine-I aldehyde is proposed as a branch point via festuclavine or pyroclavine to clavine-type alkaloids in Trichocomaceae and via agroclavine to ergoamides and ergopeptines in Clavicipitaceae. Here we report the conversion of chanoclavine-I aldehyde to agroclavine by EasG from Claviceps purpurea, a homologue of the festuclavine synthase FgaFS in Aspergillus fumigatus, in the presence of reduced glutathione and NADPH. EasG comprises 290 amino acids with a molecular mass of about 31.9 kDa. The soluble monomeric His6-EasG was purified after overproduction in E. coli by affinity chromatography and used for enzyme assays. The structure of agroclavine was unequivocally elucidated by NMR and MS analyses.

Simple total syntheses of (-)-ergot alkaloids and their (+)-enantiomers by a common synthesis method utilizing optical resolution

The first and simple total syntheses of (-)-isochanoclavine-1 ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-1 ((-)-4), and (-)-norchanoclavine-1 ((-)-5c) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-1 is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-1 (1c) are also included.