Basic information
- CAS
3604-87-3- Standard SMILES
C[C@H]([C@H](O)CCC(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- InChIKey
UPEZCKBFRMILAV-JMZLNJERSA-N- Molecular formula
- C27H44O6
- Average molar mass
- 464.6 g/mol
- Monoisotopic mass
- 464.31378912
Overview
Ecdysone is a 6-oxo steroid that is 5beta-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 22 and 25 respectively (the 2beta, 3beta, 22R stereoisomer). It is a steroid prohormone of the major insect moulting hormone 20-hydroxyecdysone. It has a role as a prohormone. It is an ecdysteroid, a 3beta-sterol, a 2beta-hydroxy steroid, a 14alpha-hydroxy steroid, a 22-hydroxy steroid, a 25-hydroxy steroid and a 6-oxo steroid. It derives from a hydride of a 5beta-cholestane.
Names & identifiers
- Preferred name
- Ecdysone
- IUPAC
- (2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
- English name
- Ecdysone
- Molecular formula
- C27H44O6
- Molecular weight
- 464.63
Names & synonyms
ECDYSONE(2beta,3beta,5beta,22R)-2,3,14,22,25-Pentahydroxycholest-7-en-6-oneRH692X7B7BCHEBI:166882beta,3beta,14alpha,22R,25-pentahydroxy-5beta-cholest-7-en-6-one(22R)-2beta,3beta,14alpha,22,25-pentahydroxy-5beta-cholest-7-en-6-oneCholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2beta,3beta,5beta,22R)-(2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one(2S,3R,5R,9R,10R,13R,14S,17R)-17-((2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-6-oneRefChem:136201222-760-43604-87-3
Show more names
α-EcdysoneA-ECDYSONEEcdyteroneALPHA-ECDYSONALPHA-ECYSONEECDYSONE, ALPHA-ALPHA-ECDYSTERONEEcdysone USP/EP/BP
alpha-Ecdysone5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)-a-Ecdysone ( >90%)CCRIS 6931EINECS 222-760-4BRN 2422986UNII-RH692X7B7B(2ss,3ss,5ss,22R)-2,3,14,22,25-pentahydroxycholest-7-en-6-one
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 118 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 821
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Physicochemical properties
- Melting point
- 242 °C · 242°C
- alpha
- 20578 · 20578 +62°
- Boiling point
- 488.1 °C · 488.1°C (rough estimate)
- Density
- 1.0493 · 1.0493 (rough estimate)
- refractive index
- 1.4482 · 1.4482 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Very Slightly, Heated)
- form
- Solid
- pka
- 14.07 · 14.07±0.70(Predicted)
- color
- White to Off-White
- optical activity
- 5820 · +5820 (c 0.1, ethanol)
- Merck
- 13 · 13,3525
- BRN
- 2422986 · 2422986
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- F
- 10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- FZ8170000
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionEcdysterone, also known as ecdysone or β-ecdysone, is a hormone that regulates the growth and development of insects. In 1954, Butenandt et al. isolated 250mg of the initial insect metamorphic active substance, ecdysone, from 500kg of silkworm pupae. Since then, various similar substances have been isolated from many plants. It has been found that ecdysteroids are not only more abundant in the plant kingdom compared to the animal kingdom, but also widely distributed and abundant in resources. Examples of ferns that contain ecdysteroids include Chinese cornbind, Sichuan cornbind, mulberry leaves, Dectenium heterocarpon, water plantain, Ginkgo biloba, yew, Thelypteris palustris, and Cyrtomium falcatum, among others.
Usesα-Ecdysone is a steroidal prohormone.
Suppliers89 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
Hebei baicao biology science and technology co., ltd+86-19131911055 17824879454 · [email protected]
Shaanxi LonierHerb Bio Technology Co Ltd+86-86-+86-86-029-87551862 15002946897 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Shenzhen Monkono Technology Co.,Ltd+86-17063441314 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
西安久启生物科技有限公司18729366352 13186100227 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017; +8613259417953 · [email protected]
Related reactions
0 records
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Compound notes
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