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

• ChemBase ID: 126618
• Molecular Formular: C13H14O5
• Molecular Mass: 250.24726
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid
• IUPAC Traditional name: antimycin
• Synonyms: 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; 桔青霉素; 桔霉素

Database IDs

• CAS Number: 518-75-2
• EC Number: 208-257-2
• MDL Number: MFCD00006912
• Beilstein Number: 5282243
• PubChem SID: 162220948; 24892302
• PubChem CID: 54680783
• CHEMBL: 510139
• Chemspider ID: 10222475
• KEGG ID: C16765
• Unique Ingredient Identifier: 3S697X6SNZ
• Wikipedia Title: Citrinin

CALCULATED PROPERTIES

• Acid pKa: 3.9141996
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.78353536
• LogD (pH = 7.4): -2.4344025
• Log P: 0.8089524
• Molar Refractivity: 65.2535 cm^3
• Polarizability: 24.46187 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Insoluble in water; Methanol
• Apperance: Lemon-yellow needles; Yellow Solid
• Melting Point: >135°C (dec.); 175 °C (''decomp.'')

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: DJ2275000
• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-40
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331-H351
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC); ≥98.0% (TLC); 98%
• Biological Source: from Penicillium citrinum
• Empirical Formula (Hill Notation): C13H14O5

DETAILS

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.

REFERENCES

• 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)