Citrinin - Moligand™, ≥98% , CAS No.518-75-2

CAS: 518-75-2 Cat. No.: C113853 分子式: C₁₃H₁₄O₅ 分子量: 250.25 Beilstein Registry Number: 5282243 EC番号: 208-257-2

GRADE & PURITY Moligand™, ≥98%

Synonyms

HY-101232 | (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid | CITRININ [MI] | CHEBI:48707 | KBioSS_000931 | Citrinin, 98% | KBio2_003499 | (3R-trans)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carbox

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

概要

Citrinin is a mycotoxin capable of inducing mitochondrial permeability transition. Citrinin also inhibits microtubule polymerization

Specifications

同義語

HY-101232 | (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid | CITRININ [MI] | CHEBI:48707 | KBioSS_000931 | Citrinin, 98% | KBio2_003499 | (3R-trans)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carbox

仕様と純度

Moligand™, ≥98%

生化学的・生理学的メカニズム

Mycotoxin. Tubulin polymerization inhibitor. Prevents mitotic spindle formation. Induces cell cycle arrest at G2/M phase and apoptosis. Shows nephrotoxic effects in vivo. Orally active.

保管条件

Store at -20°C,Argon charged

入荷

Ice chest + Ice pads

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

等級

Moligand™

注

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

純度

≥98%

名前と識別子

• パブケム・シド: 528772287
• カノニカル・スマイル: CC1C(OC=C2C1=C(C(=C(C2=O)C(=O)O)O)C)C
• IUPAC Name: (3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydroisochromene-7-carboxylic acid
• InChIKey: CBGDIJWINPWWJW-IYSWYEEDSA-N
• INCHI: 1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,14H,1-3H3,(H,16,17)/t5-,7-/m1/s1
• 異性体SMILES: C[C@@H]1[C@H](OC=C2C1=C(C(=C(C2=O)C(=O)O)O)C)C
• WGKドイツ: 3
• RTECS: DJ2275000
• UN番号: 3462
• 分子量: 250.25
• Beilstein: 5282243
• Reaxy-Rn: 7975720
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7975720&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • 分類 Benzopyrans

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• 分類: Benzopyrans
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzopyrans
• Alternative Parents: Vinylogous esters Vinylogous acids Ketones Oxacyclic compounds Monocarboxylic acids and derivatives Enols Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Benzopyran - Vinylogous ester - Vinylogous acid - Ketone - Oxacycle - Monocarboxylic acid or derivatives - Enol - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• 説明: This compound belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

化学的性質と物理的性質

• 溶解度: Slightly soluble in water. Soluble in dilute alkaline solutions. Soluble in methanol, ethanol, acetonitrile
• 感度: light sensitive & Moisture sensitive
• 融点（°C）: 170-179°C
• 分子量: 250.250 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 250.084 Da
• Monoisotopic Mass: 250.084 Da
• Topological Polar Surface Area: 83.800 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 536.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

参考文献

1. Qian Yang, Yanjing Guo, He Wang, Zhi Luo, Ying Chen, Mengyun Jiang, Huan Lu, Bernal E. Valverde, Sheng Qiang, Reto Jörg Strasser, Shiguo Chen.  (2023)  Action of the fungal compound citrinin, a bioherbicide candidate, on photosystem II.  PEST MANAGEMENT SCIENCE,  80  (1): (133-148).  [PMID:37103431] [10.1002/ps.7513]

2. Hu Xiaopeng, Xia Yide, Liu Yiwei, Zhao Faqiong, Zeng Baizhao.  (2021)  Determination of patulin using dual-dummy templates imprinted electrochemical sensor with PtPd decorated N-doped porous carbon for amplification.  MICROCHIMICA ACTA,  188  (5): (1-9).  [PMID:33797604] [10.1007/s00604-021-04812-2]

3. Li Z., Liu Y., Li Y., Lin F., Wu L..  (2020)  Screening and identification of Monascus strains with high‐yield monacolin K and undetectable citrinin by integration of HPLC analysis and pksCT and ctnA genes amplification.  JOURNAL OF APPLIED MICROBIOLOGY,  129  (5): (1410-1418).  [PMID:32357272] [10.1111/jam.14689]

4. Yanqing Liu, Hongwu Wang, Su Yao, Peijie Zhu.  (2018)  Detection of trace amounts of citrinin in dried orange peel by using an optimized extraction method coupled with ultra-performance liquid chromatography–tandem mass spectrometry.  BIOMEDICAL CHROMATOGRAPHY,  32  (8): (e4237).  [PMID:29517126] [10.1002/bmc.4237]

5. Hongcheng Gao, Zhenzhen Xie, Shihao Xu, Changlong Jiang.  (2025)  MUA-modified Au nanocluster-driven fluorescence sensor for chromatographic test strips-based visual detection of patulin.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:39826168] [10.1016/j.saa.2025.125736]

6. Sai Zhang, Ruixi Yang, Yaping Wang, Qinqin Gao, Langhong Wang, Guisheng Zhou, Qinglin Sheng.  (2024)  Multifunctional fluorescence sensor based on nitrogen-doped carbon dots and its application for toxoflavin detection.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.112168]

7. Hai Chi, Yue Xiao, Xuefei Wen, Houqi Ning, Xingzhong Zhang, Hongrui Chen, Jie Tang.  (2025)  An electrochemical sensor employing a molecularly imprinted-aptamer synergistic recognition strategy based on Cu-Zr bimetallic MOF-818 for the highly sensitive detection of zearalenone.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.107243]

8. Tao Liao, Dan Hou, Hao Huang, María Belén Camarada, Xiaoning Liao.  (2025)  A novel ratiometric molecularly imprinted electrochemical sensor based on Ag and ionic liquid co-functionalized MXene for highly sensitive and selective detection of patulin.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2025.138943]

9. Yifei He, Xiaoshuo Zhang, Lei Shi, Baizhao Zeng.  (2025)  Preparation of a low-toxic biomass-derived carbon dots-based magnetic molecular imprinting electrochemiluminescence sensor for the rapid separation and highly sensitive detection of zearalenone.  FOOD CHEMISTRY,      [PMID:41317587] [10.1016/j.foodchem.2025.147330]

10. Xiao Yue, Wen Xuefei, Zhang Xingzhong, Chen Hongrui, Tang Jie, Chi Hai, Li Liman, Thanapop Soteyome.  (2026)  Dual-functional monomers synergistically facilitate the assembly of a CoNiZn@C-based molecularly imprinted electrochemical sensor for highly sensitive detection of zearalenone.  MICROCHIMICA ACTA,  193  (7): (503).  [PMID:] [10.1007/s00604-026-08220-2]