Hydroxyecdysone

Names

[ Name ]:
Hydroxyecdysone

[Synonym ]:
CRUSTECDYSONE
20-hydroxyecdysone
MFCD00036740
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-Trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methyl-2-heptanyl]-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-on
β-ecdysone
(2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
Cholest-7-en-6-one, 2,3,14,20,22,25-hexahydroxy-, (2β,3β,5β,22R)-
Hydroxyecdysone
b-Ecdysone
Isoinokosterone
Commisterone
(2b,3b,5b,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
Ecdysterone
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-Trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methyl-2-heptanyl]-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one

Biological Activity

[Description]:

Crustecdysone (20-Hydroxyecdysone) is a naturally occurring ecdysteroid hormone isolated from Cyanotis arachnoides C.B.Clarke which controls the ecdysis (moulting) and metamorphosis of arthropods, it inhibits caspase activity and induces autophagy via the 20E nuclear receptor complex, EcR-USP[1].Crustecdysone exhibits regulatory or protective roles in the cardiovascular system[2].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Apoptosis >> Caspase

Signaling Pathways >> Autophagy >> Autophagy

[References]

[1]. Liu H, et al. E93 predominantly transduces 20-hydroxyecdysone signaling to induce autophagy and caspase activity in Drosophila fat body. Insect Biochem Mol Biol. 2014 Feb;45:30-9.

[2]. Phungphong S, et al. 20-Hydroxyecdysone attenuates cardiac remodeling in spontaneously hypertensive rats. Steroids. 2017 Oct;126:79-84.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
702.1±60.0 °C at 760 mmHg

[ Melting Point ]:
242-244 °C

[ Molecular Formula ]:
C₂₇H₄₄O₇

[ Molecular Weight ]:
480.634

[ Flash Point ]:
392.4±29.4 °C

[ Exact Mass ]:
480.308716

[ PSA ]:
138.45000

[ LogP ]:
-0.53

[ Vapour Pressure ]:
0.0±5.0 mmHg at 25°C

[ Index of Refraction ]:
1.597

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
alcohol: soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ8060000

CHEMICAL NAME :: 5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,20,22,25-hexahydroxy-, (22R)-

CAS REGISTRY NUMBER :: 5289-74-7

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C27-H44-O7

MOLECULAR WEIGHT :: 480.71

WISWESSER LINE NOTATION :: L E5 B666 LV JUTJ A1 E1 FXQ1&YQ2XQ1&1 IQ OQ PQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >9 gm/kg

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

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6400 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 350 ug/kg

SEX/DURATION :: male 7 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 100 nmol/L

REFERENCE :: ENZYAS Enzymologia. (The Hague, Netherlands) V.1-43, 1936-72. Volume(issue)/page/year: 41,183,1971

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
FZ8060000

[ Packaging Group ]:
II; III

[ Hazard Class ]:
4.1

[ HS Code ]:
2937290090

Customs

[ HS Code ]: 2937290090

Articles

Functions of nuclear receptor HR3 during larval-pupal molting in Leptinotarsa decemlineata (Say) revealed by in vivo RNA interference.

Insect Biochem. Mol. Biol. 63 , 23-33, (2015)

Our previous results revealed that RNA interference-aided knockdown of Leptinotarsa decemlineata FTZ-F1 (LdFTZ-F1) reduced 20E titer, and impaired pupation. In this study, we characterized a putative ...

Identification of two juvenile hormone inducible transcription factors from the silkworm, Bombyx mori.

J. Insect Physiol. 80 , 31-41, (2015)

Juvenile hormone (JH) regulates many physiological processes in insects. However, the signal cascades in which JH is active have not yet been fully elucidated, particularly in comparison to another ma...

A view through a chromatin loop: insights into the ecdysone activation of early genes in Drosophila.

Nucleic Acids Res. 42(16) , 10409-24, (2014)

The early genes are a key group of ecdysone targets that function at the top of the signaling hierarchy. In the presence of ecdysone, early genes exhibit a highly characteristic rapid and powerful ind...

Related Compounds

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