(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid

• ChemBase编号: 126618
• 分子式: C13H14O5
• 平均质量: 250.24726
• 单一同位素质量: 250.08412355
• SMILES: O=C1C(=C(O)C2=CO[C@H](C)[C@@H](C)C2=C1C)C(=O)O
• Canonical SMILES: C[C@H]1OC=C2C(=C(C)C(=O)C(=C2O)C(=O)O)[C@@H]1C
• InChI: InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1
• InChIKey: CQIUKKVOEOPUDV-IYSWYEEDSA-N

名称和登记号

名称

• IUPAC标准名: (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid
• IUPAC传统名: antimycin
• 别名: 桔青霉素; 桔霉素; Antimycin; Citrinin; 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid; Citrinin; (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic Acid; (3R-trans)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic Acid; Citrinin; NSC 186; (-)-Citrinin

登记号

• CAS号: 518-75-2
• EC号: 208-257-2
• MDL号: MFCD00006912
• Beilstein号: 5282243
• PubChem SID: 162220948; 24892302
• PubChem CID: 54680783
• CHEMBL: 510139
• Chemspider ID: 10222475
• KEGG ID: C16765
• 美国药典/FDA物质标识码: 3S697X6SNZ
• 维基百科标题: Citrinin

理论计算性质

• Acid pKa: 3.9141996
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): -0.78353536
• LogD (pH = 7.4): -2.4344025
• Log P: 0.8089524
• 摩尔折射率: 65.2535 cm^3
• 极化性: 24.46187 Å^3
• 极化表面积: 83.83 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Insoluble in water; Methanol
• 外观: Lemon-yellow needles; Yellow Solid
• 熔点: >135°C (dec.); 175 °C (''decomp.'')

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS编号: DJ2275000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 3462
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 23/24/25-40
• 安全公开号: 26-36/37/39-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H311-H331-H351
• GHS警示性声明: P261-P280-P301 + P310-P311
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (TLC); ≥98.0% (TLC); 98%
• 生物来源: from Penicillium citrinum
• Empirical Formula (Hill Notation): C13H14O5

详细说明

Sigma Aldrich - 00302

Biochem/physiol Actions
A mycotoxin found in grains and animal feed that nephrotoxic and is a teratogen in rodents, reducing blastocyst cell number, embryonic survival, and neonatial weight and increasing fetal abnormalities. It′s cytotoxicity to cells in culture are associated with the production of reactive oxygen species, the activation of mitochondrial apoptotic pathways, and the inhibition of antiapoptotic phosphorylation pathways.

Toronto Research Chemicals - C523500

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.

参考文献

• Ciegler, A., et al.: Appl. Microbiol., 26, 271 (1973)
• Creppy, E., et al.: Toxicol. Lett., 28, 29 (1973)
• DeGroene, E., et al.: Cancer Res., 56, 299 (1973)