20-Hydroxyecdysone β-蜕皮甾酮

CAS 5289-74-7 MFCD00036740

化学结构图

5289-74-7
SMILES: CC(C)(O)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

化学属性

Mol. FormulaC27H44O7
Mol. Weight481
Melting Point242-244°C
Appearance powder
Solubilityalcohol: soluble
Density1.28
Boiling Point702.1°C at 760 mmHg
Flash Point392.3°C

别名和识别编码

Chemical Name20-Hydroxyecdysone
Synonym 2β,3β,14α,20β,22,25-Hexahydroxy-7-cholesten-6-one 2,3,14,20 20-HYDROXYECDYSON 20-Hydroxyecdysone; 2b,3b,14a,20b,22,25-Hexahydroxycholest-7-en-6-one; beta-Ecdysone 20-羟基蜕皮素 20-羟基蜕皮酮 BETA-ECDYSONE Crustecdysone HYDROXYECDYSONE, 20- Insect moulting hormone beta-蜕皮甾酮 {} {} {uni_hamburg} Ecdysterone {} {} {} {Chemicalbook} ECDYSONE, BETA- β-Ecdyson β-Ecdysone 2β,3β,14α,20β,22,25-Hexahydroxy-7-cholesten-6-one Ecdysterone Insect moulting hormone Polypodine A β-Ecdysone, 2β,3β,14α,20β,22,25-Hexahydroxy-7-cholesten-6-one, Ecdysterone, Insect moulting hormone, Polypodine A β-Ecdysterone 脱皮激素 脱皮甾酮 脱皮甾酮(蜕皮激素) 蓝耳草甾酮
MDL NumberMFCD00036740
PubChem Substance ID5459840
Beilstein Registry Number1917578
CAS Number5289-74-7
Chemical Name Translationβ-蜕皮甾酮
Merck Number3491
Reaxys-RN1917578
Wiswesser Line NotationL E5 B666 LV JUTJ A1 E1 FXQ1&YQ2XQ1&1 IQ OQ PQ
LabNetwork Molecule IDLN00350940
InChIInChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1
Canonical SMILESO[C@@H]1[C@H](O)C[C@](C(C=C2[C@]3([H])CC[C@@]4(C)[C@@]2(O)CC[C@]4([H])[C@](O)(C)[C@H](O)CCC(O)(C)C)=O)([H])[C@]3(C)C1
EC Number
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分类

  • {SNA} Analytical Standards, Analytical/Chromatography, Bioactive Small Molecules, Cell Signaling and Neuroscience, Chromatography, Cytokines, Growth Factors and Hormones, Environmental Standards, Growth regulators, H, Hormones, Insecticides, Nutrition Research, Other Steroid Products, Pesticides, Pesticides & Metabolites, Phytochemicals by Chemical Classification, Steroid, Steroid Hormones, 细胞生物学
  • {SNA} Analytical Standards, Analytical/Chromatography, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
  • {SNA} Analytical Standards, Analytical/Chromatography,
  • {

产品应用

  • 在昆虫生长、发育、细胞扩增和凋亡中其关键作用，靠调控基因表达调控蜕皮和变态。

相关文献及参考

  • [2]. Phungphong S, et al. 20-Hydroxyecdysone attenuates cardiac remodeling in spontaneously hypertensive rats. Steroids. 2017 Oct;126:79-84.
  • [3]. Minglei Lu, et al. Ecdysone Elicits Chronic Renal Impairment via Mineralocorticoid-Like Pathogenic Activities. Cell Physiol Biochem. 2018;49(4):1633-1645.
  • Aldaz, S., et al., Live Imaging Of Drosophila Imaginal Disc Development. Proc. Natl. Acad. Sci. U. S. A. 107 , 14217-22, (2010) 摘要
  • Baehrecke, E.H., Ecdysone signaling cascade and regulation of Drosophila metamorphosis. Arch. Insect Biochem. Physiol. 33 , 231-244, (1996) 摘要
  • Buszczak, M., and Segraves, W.A., Drosophila metamorphosis: the only way is USP? Curr. Biol. 8 , R879-R882, (1998) 摘要
  • Champlin, D.T., and Truman, J.W., Ecdysteroid control of cell proliferation during optic lobe neurogenesis in the moth Manduca sexta . Development 125 , 269-277, (1998) 摘要
  • Hodin, J., and Riddiford, L.M., The ecdysone receptor and ultrasp

安全信息

WGK Germany2
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Safety Statements
RTECSFZ8060000
GHS Symbol
Storage condition 2-8°C <0°C 贮存温度-20℃
Hazard Class9
UN Number 3077
Signal word
Precautionary statements
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
Packing GroupIII 
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
REFERENCE :
   NYKZAU Nippon Yakurigaku Zasshi.  Japanese Journal of Pharmacology. (Nippon
   Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho,
   Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40-    1944- Volume(issue)/page/year:
   66,551,1970

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
REFERENCE :
   NYKZAU Nippon Yakurigaku Zasshi.  Japanese Journal of Pharmacology. (Nippon
   Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho,
   Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40-    1944- Volume(issue)/page/year:
   66,551,1970

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

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Insect - not otherwise specified Cells - not
                          otherwise specified
DOSE/DURATION           : 10400 nmol/L
REFERENCE :
   CNJGA8 Canadian Journal of Genetics and Cytology.  (National Research
   Council of Canada, Publication Sales and Distribution, Ottawa ON K1A OR6,
   Canada)  V.1-    1959-  Volume(issue)/page/year: 24,27,1982

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - mouse Liver
DOSE/DURATION           : 100 nmol/L
REFERENCE :
   ENZYAS Enzymologia.  (The Hague, Netherlands)  V.1-43, 1936-72.
   Volume(issue)/page/year: 41,183,1971

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Parenteral
TEST SYSTEM             : Insect - Drosophila melanogaster
DOSE/DURATION           : 300 umol/L
REFERENCE :
   NNBYA7 Nature (London), New Biology.  (Basingstoke, Hants., UK)  V.229-246,
   1971-73.  For publisher information, see NATUAS.  Volume(issue)/page/year:
   230,222,1971

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Parenteral
TEST SYSTEM             : Insect - silkworm
DOSE/DURATION           : 100 umol/L
REFERENCE :
   ENZYAS Enzymologia.  (The Hague, Netherlands)  V.1-43, 1936-72.
   Volume(issue)/page/year: 41,183,1971

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Mammal - species unspecified Liver
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   ENZYAS Enzymologia.  (The Hague, Netherlands)  V.1-43, 1936-72.
   Volume(issue)/page/year: 41,183,1971

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
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
REFERENCE :
   NYKZAU Nippon Yakurigaku Zasshi.  Japanese Journal of Pharmacology. (Nippon
   Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho,
   Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40-    1944- Volume(issue)/page/year:
   66,551,1970

Hazard Codes
Risk Statements

其他信息

  • 用途一:在昆虫生长、发育、细胞扩增和凋亡中其关键作用，靠调控基因表达调控蜕皮和变态。
  • Sigma Aldrich:5289-74-7(sigmaaldrich)
  • MSDS 信息:20-Hydroxyecdysone(5289-74-7).msds
  • MOL 文件:5289-74-7.mol
  • color:white
  • F:10

系列性分类

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Pyrroles 吡咯
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Pyrroles 吡咯
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Cytokines, Growth Factors and Hormones - Cell Signaling and Neuroscience
  5. Hormones - Cytokines, Growth Factors and Hormones
  6. Steroid Hormones - Hormones
  7. Other Steroid Products - Steroid Hormones
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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