Basic information
- CAS
90-65-3- Standard SMILES
C=C(C)C(=O)C(=CC(=O)O)OC- InChIKey
VOUGEZYPVGAPBB-UHFFFAOYSA-N- Molecular formula
- C8H10O4
- Average molar mass
- 170.16 g/mol
- Monoisotopic mass
- 170.0579088
Overview
(EZ)-penicillic acid has been reported in Penicillium cyclopium, Penicillium baarnense, and other organisms with data available.
Names & identifiers
- Preferred name
- 3-Methoxy-5-methyl-4-oxohexa-2,5-dienoic acid
- IUPAC
- 3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid
- English name
- Penicillic acid
- Molecular formula
- C8H10O4
- Molecular weight
- 170.16
Names & synonyms
3-Methoxy-5-methyl-4-oxohexa-2,5-dienoic acidSCHEMBL148669NSC 402844; (E)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acidVOUGEZYPVGAPBB-UHFFFAOYSA-NAKOS028110678BP162741NS00004523NSC 402844pencillicacidPENICILLINACIDPenicillic acidkyselinapenicilova
Show more names
Penicillic acid,99%PENICILLIC ACID 99%Penicillic acid, 99% 25MGPenicillic Acid in MethanolBenzylpenicillin Impurity 26
Database identifiers
- CAS
90-65-3- PubChem CID
- 7025
- DTXSID
DTXSID1074830
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 63.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 250
Physicochemical properties
- Melting point
- 83 · 83-87 °C
- Boiling point
- 219.79 °C · 219.79°C (rough estimate)
- Density
- 1.1456 · 1.1456 (rough estimate)
- refractive index
- 1.4425 · 1.4425 (estimate)
- storage temp.
- 2 · Store at 2-8
- solubility
- 10 mg/mL · DMSO: >10mg/mL
- pka
- 3.9 · 3.90±0.33(Predicted)
- form
- solid
- color
- Needles from pet ether or rhombic orhexagonal plates
- Merck
- 13 · 13,7163
- CAS DataBase Reference
- 90 · 90-65-3
- FDA UNII
- 14 K3AFD · ONL14K3AFD
- IARC
- 3 · 3 (Vol. 10, Sup 7) 1987
- EPA Substance Registry System
- Penicillic acid (90-65-3)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- rtecs
- MM2625000
- ridadr
- 2811
- hs_code
- 29189900
- Toxicity
- LD50 i.p. in mice: 90.00 mg/kg (Chan et al.)
- risk_code
- 36/37/38-20/21/22-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T
- safety_code
- 37/39-26-24/25
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard statements
- H302
- Precautionary statements
- P271-P260
- Hazardous Substances Data
- 90-65-3(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionGram negative bacteria utilize N-acylated homoserine lactones to coordinate expression of virulence in response to the density of the surrounding bacterial population in a process termed quorum sensing. By interfering with this communication and thereby disrupting virulence expression, quorum sensing inhibitors are emerging as an alternative to the conventional ways of fighting bacterial infections. Penicillic acid is a mycotoxin produced from Penicillium species identified in molds on corn and other grains. At 80 μM, penicillic acid inhibits bacterial quorum sensing communication in P. aeruginosa by selectively repressing various virulence factor and other quorum sensing-regulated genes. It has been shown to inhibit Fas-mediated apoptosis at 100-200 μM by targeting caspase-8 activity in Burkitt’s lymphoma Raji cells.
UsesGram negative bacteria utilize N-acylated homoserine lactones to coordinate expression of virulence in response to the density of the surrounding bacterial population in a process termed quorum sensing. By interfering with this communication and thereby disrupting virulence expression, quorum sensing inhibitors are emerging as an alternative to the conventional ways of fighting bacterial infections. Penicillic acid is a mycotoxin produced from Penicillium species identified in molds on corn and other grains. At 80 μM, penicillic acid inhibits bacterial quorum sensing communication in P. aeruginosa by selectively repressing various virulence factor and other quorum sensing-regulated genes. It has been shown to inhibit Fas-mediated apoptosis at 100-200 μM by targeting caspase-8 activity in Burkitt’s lymphoma Raji cells.
UsesPenicillic acid can be isolated from the seed-borne fungus Aspergillus persii EML-HPB1-11 and it exhibits antibacterial activity against various plant pathogenic bacteria. This compound can be a potential lead molecule for developing synthetic agrochemicals. Penicillic acid is also used as a quorum sensing inhibitor.
Suppliers52 total
北京华美互利生物化工010-56205725 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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