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Tenuazonic acid

Tenuazonic acid structure

CAS No:
610-88-8
Formula:
C10H15NO3
Chemical Name:
Tenuazonic acid
Synonyms:
2H-Pyrrol-2-one,3-acetyl-1,5-dihydro-4-hydroxy-5-[(1S)-1-methylpropyl]-,(5S)-;3-Pyrrolin-2-one,3-acetyl-5-sec-butyl-4-hydroxy-,L-;2H-Pyrrol-2-one,3-acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-,[S-(R*,R*)]-;Tenuazonic acid;(5S)-3-Acetyl-1,5-dihydro-4-hydroxy-5-[(1S)-1-methylpropyl]-2H-pyrrol-2-one;L-Tenuazonic acid;AAC-toxin;128892-49-9;16818-18-1
Categories:
Analytical Chemistry > Standard

Description

Tenuazonic acid, belonging to tetramic acids that are the largest family of natural products, is a putative nonhost-selective mycotoxin isolated from Alternaria alternate[1]. Tenuazonic acid blocks electron transport beyond primary quinone acceptor (QA) by interacting with D1 protein and it is a broad-spectrum and effective photosystem II (PSII) inhibitor[2].

Solid

3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one. A metabolite found in a strain of the fungus Alternaria tenuis Auct. which functions as an antibiotic with antiviral and antineoplastic properties, and may also act as a mycotoxin.

Tenuazonic acid Basic Attributes

Molecular Weight：

83.0886

Exact Mass：

197.23

HScode：

29337900

Characteristics

PSA：

66.40000

XLogP3：

0.81

Appearance：

Solid

Density：

1.2±0.1 g/cm3

Melting Point：

74-76 °C

Boiling Point：

bp0.035 117°

Flash Point：

196.4±28.7 °C

Refractive Index：

1.519

Storage Conditions：

2-8°C

Specific rotation：

20D -128° (c = 1.0 in methanol); -132 ± 2° (c = 0.5 in CHCl3)

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

RTECS Number：

UY7425000

Marks：

Precautionary statement(s)：

P301 + P310

Hazard Statements：

H301

GHS Classification：

|Danger|H301 (97.44%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)|Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

MeSH Entry Terms：

Acid, Tenuazonic

Tenuazonic acid Use and Manufacturing

An alternaria mycotoxin, found in common edible crops.It inhibits protein synthesis in fibroblasts.

Computed Properties

Molecular Weight:197.23
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:197.10519334
Monoisotopic Mass:197.10519334
Topological Polar Surface Area:66.4
Heavy Atom Count:14
Complexity:307
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes