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Ergosterol endoperoxide

Names

[ CAS No. ]:
2061-64-5

[ Name ]:
Ergosterol endoperoxide

[Synonym ]:
5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol
Ergosterol peroxide
Peroxyergosterol
(3S,5S,8S,9R,10R,13R,14R,17R)-17-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol
3b,5a-Etheno-1H-benz[c]indeno[5,4-e][1,2]dioxin-7-ol, 2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-9a,11a-dimethyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-, (1R,3aR,3bS,5aS,7S,9aR,9bR,11aR)-
UNII:UG9TN81TGH
Ergosterol endoperoxide
(1S,2R,5R,6R,9R,10R,13S,15S)-5-[(2R,3E,5R)-5,6-Dimethyl-3-hepten-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0.0.0]nonadec-18-en-13-ol
Ergosterol 5.alpha.,8.alpha.-epidioxide
Ergosterol 5.α.,8.α.-epidioxide
ergosterol-5,8-peroxide
5α,8α-Ergosta-6,22-dien-3β-ol, 5,8-epidioxy-

Biological Activity

[Description]:

Ergosterol peroxide is a steroid derivative and can be isolated from a variety of fungi, yeast, lichens or sponges. Ergosterol peroxide has anti-tumour, proapoptotic, anti-inflammatory, anti-mycobacterial, and anti-proliferative activities[1][2].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Inflammation/Immunology
Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Ming Bu, et al. Synthesis of Ergosterol Peroxide Conjugates as Mitochondria Targeting Probes for Enhanced Anticancer Activity. Molecules. 2019 Sep 11;24(18):3307

[2]. Taotao Ling, et al. Development of ergosterol peroxide probes for cellular localisation studies. Org Biomol Chem. 2019 May 29;17(21):5223-5229.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
499.7±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C28H44O3

[ Molecular Weight ]:
428.647

[ Flash Point ]:
256.0±28.7 °C

[ Exact Mass ]:
428.329041

[ PSA ]:
38.69000

[ LogP ]:
7.68

[ Vapour Pressure ]:
0.0±2.9 mmHg at 25°C

[ Index of Refraction ]:
1.552

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KE7289000
CHEMICAL NAME :
5-alpha,8-alpha-Ergosta-6,22-dien-3-beta-ol, 5,8-epidioxy-
CAS REGISTRY NUMBER :
2061-64-5
BEILSTEIN REFERENCE NO. :
0096852
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C28-H44-O3
MOLECULAR WEIGHT :
428.72

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
30 mg/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
REFERENCE :
JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 46,461,1976
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
60 mg/kg
SEX/DURATION :
female 6-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 46,461,1976

Safety Information

[ Hazard Codes ]:
Xi

Precursor & DownStream

Precursor

DownStream

Related Compounds