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(R)-Usnic acid

(R)-Usnic acid structure

CAS No:
7562-61-0
Formula:
C18H16O7
Chemical Name:
(R)-Usnic acid
Synonyms:
1,3(2H,9bH)-Dibenzofurandione,2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-,(9bR)-;Usnic acid,(R)-;(9bR)-2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione;(+)-Usninic acid;d-Usnic acid;d-Usninic acid;(+)-Usnic acid;NSC 685596;(R)-Usnic acid;(9BR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione;1414-34-2
Categories:
Natural Products > Phenols

Description

(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1].

Usnic acid is a member of the class of dibenzofurans that is dibenzo[b,d]furan-1(9bH)-one substituted by acetyl groups at positions 2 and 6, hydroxy groups at positions 3 and 7 and methyl groups at positions 8 and 9b. It has a role as an antifungal agent, a lichen metabolite and an acaricide. It is a member of dibenzofurans, a methyl ketone and a polyphenol.

(R)-Usnic acid Basic Attributes

Molecular Weight：

344.32

Exact Mass：

344.32

EC Number：

231-456-0

HScode：

2917399090

Characteristics

PSA：

121

XLogP3：

2.12660

Density：

1.5±0.1 g/cm3

Melting Point：

206 °C

Boiling Point：

605.4°C at 760 mmHg

Flash Point：

236.0±25.0 °C

Refractive Index：

1.679

Water Solubility：

Partly soluble in water. soluble in acetone, ethanol, chloroform and furfural.

Storage Conditions：

2-8°C

Specific rotation：

488 º (c=0.4, CHCl3)

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

RTECS Number：

HP5295050

Marks：

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 43 companies from 1 notifications to the ECHA C&L Inventory.

(R)-Usnic acid Use and Manufacturing

Usnic acid is used as fragrance; preservative in deodorants; in anti ac ne formulations; antibiotic for topical application.

Computed Properties

Molecular Weight:344.3
XLogP3:2.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:344.08960285
Monoisotopic Mass:344.08960285
Topological Polar Surface Area:121
Heavy Atom Count:25
Complexity:734
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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