CITRININ

Base Information

• Chemical Name: CITRININ
• CAS No.: 518-75-2
• Molecular Formula: C13H14 O5
• Molecular Weight: 250.251
• Hs Code.: 29419090
• Mol file: 518-75-2.mol

Synonyms:3H-2-Benzopyran-7-carboxylicacid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-; Citrinin(6CI); (-)-Citrinin;4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid;NSC 186

Chemical Property of CITRININ

Chemical Property:

• Appearance/Colour: yellow crystalline powder or flakes
• Vapor Pressure: 1.99E-08mmHg at 25°C
• Melting Point: 175°C (dec.)
• Refractive Index: 1.4560 (estimate)
• Boiling Point: 440.6°Cat760mmHg
• PKA: 1.52±0.60(Predicted)
• Flash Point: 170.2°C
• PSA: 83.83000
• Density: 1.37g/cm³
• LogP: 1.72100
• Storage Temp.: 2-8°C
• Solubility.: ≤2mg/ml in ethanol;20mg/ml in DMSO;20mg/ml in dimethyl formamide

Purity/Quality:

98% ^*data from raw suppliers

Citrinin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-40-36/37/38
• Safety Statements: 26-36/37/39-45-22-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Citrinin is a mycotoxin that has been found in Monascus and has diverse biological activities. It is active against S. aureus, methicillin-resistant S. aureus (MRSA), rifampicin-resistant S. aureus, and vancomycin-resistant E. faecium (MICs = 1.95, 3.9, 0.97, and 7.81 μg/ml, respectively), as well as the pathogenic yeast C. neoformans (MIC = 3.9 μg/ml). It is cytotoxic to a variety of cells in vitro, including bovine kidney cells and mice embryonic stem cells. Citrinin (30 μM) induces reactive oxygen species (ROS) production, mitochondrial membrane potential loss, and apoptosis in HepG2 cells, effects that can be blocked by the antioxidant resveratrol. In contrast, citrinin reduces glutamate-induced excitotoxicity in primary rat cortical neurons at concentrations ranging from 0.1 to 1,000 nM and inhibits LPS-induced production of nitric oxide (NO) in RAW 264.7 cells at 0.625 to 40 μM. It is toxic to brine shrimp larvae (LD50 = 96 μg/ml), as well as to rats and mice with oral LD50 values of 50 and 87-105 mg/kg, respectively. It induces reproductive abnormalities in male mice and toxic effects in the liver, kidney, heart, and gastrointestinal tracts of various animals. Citrinin has been found in stored cereal grains, as well as beans, fruit, and herbs.
• Uses: Antibiotic substance produced by a white spore aspergilus which has been placed under the species name Aspergillus niveus. Also produced in small quantities by Penicillium citrinum. antibacterial Citrinin is a quinonemethine mycotoxin produced by diverse fungi including Aspergillus and Penicillium. Citrinin has been extensively investigate, and is a potent nephrotoxin with hepatoxic and teratogenic activity. Citrinin is the causative agent of Balkan nephropathy and yellow rice fever in humans. At the molecular level, citrinin exhibits a range of effects including free radical damage to DNA and disruption of mitochondrial membrane-bound enzymic activities and structural integrity. Specifically, citrinin is an inhibitor of NADH dehydrogenase in the mitochondrial electron transport chain and this action is responsible for recent reports of citrinin's apoptotic activity.

Technology Process of CITRININ

There total 18 articles about CITRININ which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.0%

(+/-)-threo-2,6-dihydroxy-4-(2-hydroxy-1-methylpropyl)-3-methylbenzoic acid (16051-42-6,110087-26-8,112245-93-9) + orthoformic acid triethyl ester (122-51-0) → (+/-)-threo-4,6-dihydro-8-hydroxy-3,4,5-trimrthyl-6-oxo-3H-2-benzopyran-7-carboxylic acid (citrinin) (518-75-2,1086-03-9,110170-49-5,112245-94-0,136088-06-7)

Guidance literature:

With hydrogenchloride; at 0 ℃; for 0.333333h;

Reference yield:

(3R,4S)-dihydrocitrinin (3861-60-7,92838-21-6) → citrinin (518-75-2)

Guidance literature:

With palladium on activated charcoal; oxygen; nitrobenzene;

DOI:10.1021/ja01571a051

Reference yield:

(1S,2R)-2,6-dihydroxy-4-(2-hydroxy-1-methylpropyl)-3-methylbenzoic acid (163660-01-3) + orthoformic acid triethyl ester (122-51-0) → citrinin (518-75-2)

Guidance literature:

upstream raw materials:

formaldehyd

(1S,2R)-2,6-dihydroxy-4-(2-hydroxy-1-methylpropyl)-3-methylbenzoic acid

hydrogen cyanide

orthoformic acid triethyl ester

Downstream raw materials:

5-((1S,2R)-2-Hydroxy-1-methyl-propyl)-4-methyl-benzene-1,3-diol

formic acid

methylammonium carbonate

(-)-threo-3-(3,5-dimethoxy-2-methlyphenyl)butan-2-ol

Refernces

• 1、 Schwenk,Schubert,Stahl. "-". . p. 220,226. Retrieved 1949.
• 2、 Barber, Jill A.,Staunton, James,Wilkinson, Michael R.. "A Diastereoselective Synthesis of the Polyketide Antibiotic Citrinin using Toluate Anion Chemistry". . p. 2101 - 2110. Retrieved 2007/10/02.