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Alternariol

Alternariol structure

CAS No:
641-38-3
Formula:
C14H10O5
Chemical Name:
Alternariol
Synonyms:
6H-Dibenzo[b,d]pyran-6-one,3,7,9-trihydroxy-1-methyl-;Alternariol;3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one;NSC 638263;3,7,9-Trihydroxy-1-methylbenzo[c]chromen-6-one;11003-13-7
Categories:
Natural Products > Phenols

Description

Alternariol is a mycotoxin produced by Alternaria species. AOH inhibits the catalytic activity of topoisomerase I and topoisomerase II enzymes[1]. Alternariol exhibits a variety of therapeutic and biological properties such as phytotoxicity, cytotoxicity, anti-HIV, anti-cancer, and anti-microbial properties[2].

Solid

Alternariol is a benzochromenone that is 6H-benzo[c]chromen-6-one which is substituted by a methyl group at position 1 and by hydroxy groups at positions 3, 7, and 9. It is the most important mycotoxin produced by the black mould Alternaria species, which are the most common mycoflora infecting small grain cereals worldwide. It has a role as a metabolite, an EC 3.1.1.8 (cholinesterase) inhibitor and a mycotoxin. It is a benzochromenone and a member of phenols.

Alternariol Basic Attributes

Molecular Weight：

258.23

Exact Mass：

258.23

UNII：

KN9L4260JW

NSC Number：

638263

DSSTox ID：

DTXSID80214305

HScode：

29322090

Characteristics

PSA：

XLogP3：

2.93

Appearance：

Solid

Density：

1.6±0.1 g/cm3

Melting Point：

350 °C

Boiling Point：

586.9±39.0 °C at 760 mmHg

Flash Point：

232.3±20.6 °C

Refractive Index：

1.731

Water Solubility：

61.89 mg/L @ 25 °C (est)

Storage Conditions：

2-8°C

Toxicity：

Abdominal cavity-mouse LDL0: 100 mg/kg

Flammability characteristics：

Flammable; burning produces irritating fumes

Collision Cross Section：

146 Å² [M-H]- [CCS Type: TW, Method: calibrated with polyalanine]

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 3462 6.1/PG 1

wgk germany：

hazard class code：

26/27/28

safety instructions：

28-36/37/39-45

RTECS Number：

HP8757000

Marks：

T+

Storage features：

Treasury is ventilated, low temperature and dry; stored separately from food materials

Precautionary statement(s)：

P260-P264-P280-P284-P302 + P350-P310

Hazard Statements：

H300-H310-H330

GHS Classification：

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

highly toxic

Drug Information

MeSH：

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)

MeSH Entry Terms：

alternariol

Alternariol Use and Manufacturing

An alternaria mycotoxin and genotoxin, found in common edible crops.It inhibits the activity of various DNA-topoisomerases, increasing he rate of DNA strand breaks.

Computed Properties

Molecular Weight:258.23
XLogP3:2.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Exact Mass:258.05282342
Monoisotopic Mass:258.05282342
Topological Polar Surface Area:87
Heavy Atom Count:19
Complexity:371
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes