Compound: patulin
SMILES: O=C1OC2=CCOC(C2=C1)O
InChIKey: ZRWPUFFVAOMMNM-UHFFFAOYSA-N
Synonyms: patulin, 149-29-1, Clavacin, Clavatin, Patuline, Expansine, Expansin, Claviformin, Claviform, Clairformin, Leucopin, Terinin, Mycoin C3, Gigantin, Penicidin, Mycoin, Tercinin, Mycoine C3, Mycosin, Penatin, Mycoin C, 4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one, 4-hydroxy-4,6-dihydrofuro[3,2-c]pyran-2-one, 4H-Furo[3,2-c]pyran-2(6H)-one, 4-hydroxy-, 4-Hydroxy-4H-furo(3,2-C)pyran-2(6H)-one, 4H-Furo(3,2-c)pyran-2(6H)-one, 4-hydroxy-, 4,6-Dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-one, (2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone, 95X2BV4W8R, (2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid-3,4-lactone, DTXSID2021101, CHEBI:74926, Acetic acid, (2,4-dihydroxy-2H-pyran-3(6H)-ylidene)-, 3,4-lactone, NSC-8120, NSC-32951, 4H-Furo(3,3-c)pyran-2(6H)-one, 4-hydroxy-, 4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one, 2,4-Dihydroxy-2H-pyran-delta-3(6H),alpha-acetic acid-3,4-lactone, 2H-Pyran-delta(sup 3(6H),alpha)-acetic acid, 2,4-dihydroxy-, 3,4-lactone, 4-hydroxy-2H,4H,6H-furo(3,2-c)pyran-2-one, 4-hydroxy-4,6-dihydrofuro(3,2-c)pyran-2-one, RefChem:170197, DTXCID701101, EC 3.1.-, 205-735-2, Flavicin, Sch-351633, NSC 8120, NSC 32951, Patulin-13C3, MFCD00005858, NSC8120, NSC32951, SCH 351633, 748133-69-9, CHEMBL294018, Patulin 100 microg/mL in Acetonitrile, (2, 3,4-lactone, 4-Hydroxy-4,6-dihydrofuro[4,5-c]pyran-2-one, 4H-Furo[3, 4-hydroxy-, 2,.alpha.-acetic acid, 3,4-lactone, WLN: T56 BOV GO IU & TJ FQ, 247172-18-5, CCRIS 4940, HSDB 3522, SR-05000002238, EINECS 205-735-2, BRN 0149675, UNII-95X2BV4W8R, Clavicin, Clavitin, Expansion, 2H-Pyran-.delta.(sup 3(6H), 2,4-dihydroxy-, 3,4-lactone, Acetic acid,4-dihydroxy-2H-pyran-3(6H)-ylidene)-, 3,4-lactone, Gigantic acid?, Clavacin; Expansin, Patulin (Standard), DL-PATULIN, 520 - Patulin, Spectrum_000015, starbld0009637, Antibiotic YS 1649, PATULIN [HSDB], PATULIN [IARC], PATULIN [MI], Spectrum3_000796, Spectrum4_000753, Spectrum5_001659, PATULIN 13C3, Antibiotic Sch 351633, Patulin, reference material, Neuro_000008, Epitope ID:1862785, SCHEMBL29056, BSPBio_002532, KBioGR_001106, KBioSS_000355, 5-18-03-00005 (Beilstein Handbook Reference), DivK1c_000438, SPECTRUM1503904, MEGxm0_000442, orb1303540, ACon1_002106, HMS501F20, HY-N6779R, KBio1_000438, KBio2_000355, KBio2_002923, KBio2_005491, KBio3_001752, Patulin from Penicillium expansum, MSK7008, NINDS_000438, HMS1923M19, Patulin, >=98.0% (HPLC), EX-A5478, HY-N6779, YEB13369, BDBM50158841, MSK7008-100A, AKOS015904103, BS-1260, CCG-208451, DB15586, EBC-656472, FP31796, YS 1649, IDI1_000438, SMP1_000230, NCGC00095272-01, NCGC00095272-02, NCGC00095272-03, NCGC00095272-04, NCGC00095272-05, NCGC00095272-06, NCI60_041782, DB-042987, 4-Hydroxy-4H,6H-furo[3,2-c]pyran-2-one, CS-0083018, NS00011821, Patulin Solution in Acetonitrile, 100ug/mL, ST50824441, 4-Hydroxy-4H-Furo(3,3-c)pyran-2(6H)-one, A12069, 4-hydroxy-6-hydro-4H-furano[3,2-c]pyran-2-one, Q414526, 4-hydroxy-4,6-dihydro-2H-furo[3,2-c]pyran-2-one, SR-05000002238-2, SR-05000002238-3, 2,4-Dihydroxy-2H-pyran-alpha -acetic acid, 3, 4-lactone, 4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one, 9CI, 8CI, (+/-)-4-HYDROXY-4H-FURO(3,2-C)PYRAN-2(6H)-ONE, 2H-Pyran-.delta.(sup 3(6H), 2,4-dihydroxy-,3,4-lactone, 2H-Pyran-alpha )-acetic acid, 2, 4-dihydroxy-,3,4-lactone, 2H-Pyran-alpha )-acetic acid, 2,4-dihydroxy-, 3,4-lactone, 2,4-Dihydroxy-2H-pyran-.delta.-3(6H),.alpha.-acetic acid, 3,4-lactone, 2H-Pyran-.delta.(3(6H),.alpha.)-acetic acid, 2,4-dihydroxy-,3,4-lactone
Theoretical properties:
molecular_formula: C7H6O4
molecular_weight: 154.12 g/mol
exact_mass: 154.02660867 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 11
topological_polar_surface_area: 55.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Compact prisms or thick plates from ether or chloroform
color: Compact prisms or thick plates from ether or chloroform
odor: Odorless
melting_point: 111.0 °C
solubility: Soluble in ethanol, diethyl ether, acetone, benzene, and ethyl or amyl acetate
vapor_pressure: 0.0000068 [mmHg]
Descriptions:
pubchem: Patulin is a furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic. It has a role as a mutagen, a mycotoxin, an antimicrobial agent, a carcinogenic agent, an Aspergillus metabolite and a Penicillium metabolite. It is a gamma-lactone, a lactol and a furopyran.
chebi: A furopyran and lactone that is (2<em>H</em>-pyran-3(6<em>H</em>)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of <em>Aspergillus</em> and <em>Penicillium</em>, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.
chembl: PATULIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Patulin is an organic compound classified as a polyketide. It is named after the fungus from which it was isolated, Penicillium patulum. It is a white powder soluble in acidic water and in organic solvents. It is a lactone that is heat-stable, so it is not destroyed by pasteurization or thermal denaturation. However, stability following fermentation is lessened.  It is a mycotoxin produced by a variety of molds, in particular, Aspergillus and Penicillium and Byssochlamys. Most commonly found in rotting apples, the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. In addition, patulin has been found in other foods such as grains, fruits, and vegetables. Its presence is highly regulated.