agaric acid

Names

[ CAS No. ]:
666-99-9

[ Name ]:
agaric acid

[Synonym ]:
Laricic acid
n-Hexadecylcitric acid
EINECS 211-566-5
Agaricinic acid
(2S,3S)-2-Hydroxy-nonadecan-1,2,3-tricarbonsaeure
Lr-2-Hydroxy-nonadecan-1,2rF,3cF-tricarbonsaeure
Agaric acid
Agaricinsaeure
MFCD00002665
Agaricin
(2S,3S)-2-Hydroxy-nonadecan-1,2,3-tricarbonsaeure (Agaricinsaeure)
Agaricic acid
(2S,3S)-2-hydroxy-nonadecane-1,2,3-tricarboxylic acid

Biological Activity

[Description]:

Agaric acid (Agaricinic Acid) is obtained from various plants of the fungous tribe, i.e. Polyporus officinalis and Polyporus igniarius. Agaric acid induces mitochondrial permeability transition through its interaction with the adenine nucleotide translocase. Agaric acid promotes efflux of accumulated Ca2+, collapse of transmembrane potential, and mitochondrial swelling. Agaric acid is used to regulate lipid metabolism[1].

[References]

[1]. García N, et al. Agaric acid induces mitochondrial permeability transition through its interaction with the adenine nucleotide translocase. Its dependence on membrane fluidity. Mitochondrion. 2005 Aug;5(4):272-81.

Chemical & Physical Properties

[ Density]:
1.115g/cm3

[ Boiling Point ]:
509.3ºC at 760 mmHg

[ Melting Point ]:
142° (dec)

[ Molecular Formula ]:
C₂₂H₄₀O₇

[ Molecular Weight ]:
416.54900

[ Flash Point ]:
275.9ºC

[ Exact Mass ]:
416.27700

[ PSA ]:
132.13000

[ LogP ]:
4.84900

[ Index of Refraction ]:
1.501

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RA5365000

CHEMICAL NAME :: 1,2,3-Nonadecanetricarboxylic acid, 2-hydroxy-

CAS REGISTRY NUMBER :: 666-99-9

BEILSTEIN REFERENCE NO. :: 1729981

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H40-O7

MOLECULAR WEIGHT :: 416.62

WISWESSER LINE NOTATION :: QVY16&XQVQ1VQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RA5365000

Precursor & DownStream

Precursor

DownStream

Articles

Agaric acid induces mitochondrial permeability transition through its interaction with the adenine nucleotide translocase. Its dependence on membrane fluidity.

Mitochondrion 5 , 272-281, (2005)

The effect of agaric acid as inducer of mitochondrial permeability transition was studied. It was found that: (i) agaric acid (AA) promoted efflux of accumulated Ca2+, collapse of transmembrane potent...

The mechanisms of fatty acid-induced proton permeability of the inner mitochondrial membrane.

J. Bioenerg. Biomembr. 31 , 447-455, (1999)

Nonesterified long-chain fatty acids have long been known as uncouplers of oxidative phosphorylation. They are efficient protonophores in the inner mitochondrial membrane but not so in artificial phos...

The effect of N-ethylmaleimide on permeability transition as induced by carboxyatractyloside, agaric acid, and oleate.

Cell Biochem. Biophys. 51 , 81-87, (2008)

In this work, we studied the effect of N-ethylmaleimide on permeability transition. The findings indicate that the amine inhibited the effects of carboxyatractyloside and agaric acid. It is known that...