alpha-ecdysone

(2beta,3beta,5beta,22R)-2,3,14,22,25-pentahydroxycholest-7-en-6-one

CAS: 3604-87-3 C27 H44 O6 MW: 464.64288000

Identification

Namealpha-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
CAS Number3604-87-3
EINECS222-760-4
FDA UNIIRH692X7B7B
Molecular FormulaC27 H44 O6
Molecular Weight464.64288000
MDL NumberMFCD00042683
Nikkaji NumberJ8.177I
Beilstein2422986

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 632.00 °C. @ 760.00 mm Hg (est)
Flash Point 662.00 °F. TCC ( 350.00 °C. ) (est)
logP (o/w) 0.870 (est)
Soluble in water, 23.26 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for alpha-ecdysone usage levels up tonot for fragrance use.
Recommendation for alpha-ecdysone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

5-beta- cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)- cholest-7-en-6-one, 2,3,14,22,25-pentahydroxy-, (2-beta,3-beta,5-beta,22R)- (9CI) (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 a- ecdysone (2beta,3beta,5beta,22R)-2,3,14,22,25- pentahydroxycholest-7-en-6-one PubMed: Ethylparaben affects lifespan, fecundity, and the expression levels of ERR, EcR and YPR in Drosophila melanogaster. PubMed: An Adaptive Transposable Element Insertion in the Regulatory Region of the EO Gene in the Domesticated Silkworm, Bombyx mori. PubMed: Unprecedented conformational flexibility revealed in the ligand-binding domains of the Bovicola ovis ecdysone receptor (EcR) and ultraspiracle (USP) subunits. PubMed: Bisphenol A affects larval growth and advances the onset of metamorphosis in Drosophila melanogaster. PubMed: Steroid hormone (20-hydroxyecdysone) modulates the acquisition of aversive olfactory memories in pollen forager honeybees. PubMed: Changes in seasonal expression patterns of ecdysone receptor, retinoid X receptor and an A-type allatostatin in the copepod, Calanus finmarchicus, in a sea loch environment: an investigation of possible mediators of diapause. PubMed: Ecdysone receptors: from the Ashburner model to structural biology. PubMed: Receptors of garlic (Allium sativum) lectins and their role in insecticidal action. PubMed: Ecdysone receptor (EcR) suppresses lipid accumulation in the Drosophila fat body via transcription control. PubMed: 20-OH-ecdysone prevents hot flushes in ovariectomized rats. PubMed: Isoforms of the heteropteran Nezara viridula ecdysone receptor: protein characterisation, RH5992 insecticide binding and homology modelling. PubMed: Synthesis and insecticidal activity of N-tert-butyl-N,N'-diacylhydrazines containing 1,2,3-thiadiazoles. PubMed: An ecdysone receptor from the pentatomomorphan, Nezara viridula, shows similar affinities for moulting hormones makisterone A and 20-hydroxyecdysone. PubMed: Dietary hempseed meal intake increases body growth and shortens the larval stage via the upregulation of cell growth and sterol levels in Drosophila melanogaster. PubMed: Two Tor genes in the silkworm Bombyx mori. PubMed: Dietary effects of four phytoecdysteroids on growth and development of the Indian meal moth, Plodia interpunctella. PubMed: A switch in the control of growth of the wing imaginal disks of Manduca sexta. PubMed: 20-hydroxyecdysone reduces insect food consumption resulting in fat body lipolysis during molting and pupation. PubMed: An ortholog of the ecdysone receptor protein (EcR) from the parasitic nematode Haemonchus contortus. PubMed: Beneficial effects of beta-Ecdysone on the joint, epiphyseal cartilage tissue and trabecular bone in ovariectomized rats. PubMed: A second proPO present in white shrimp Litopenaeus vannamei and expression of the proPOs during a Vibrio alginolyticus injection, molt stage, and oral sodium alginate ingestion. PubMed: The TOR pathway couples nutrition and developmental timing in Drosophila. PubMed: Ecdysteroids act as inhibitors of calf skin collagenase and oxidative stress. PubMed: Diversity of detoxification pathways of ingested ecdysteroids among phytophagous insects. PubMed: Modulation of larval nutrition affects midgut neutral lipid storage and temporal pattern of transcription factor expression during mosquito metamorphosis. PubMed: Nutritional status affects 20-hydroxyecdysone concentration and progression of oogenesis in Drosophila melanogaster. PubMed: Tight transcriptional regulation of foreign genes in insect cells using an ecdysone receptor-based inducible system. PubMed: The ecdysone-induced DHR4 orphan nuclear receptor coordinates growth and maturation in Drosophila. PubMed: Chemical residues and bioactivity of tebufenozide applied to apple foliage. PubMed: Programmed autophagy in the Drosophila fat body is induced by ecdysone through regulation of the PI3K pathway. PubMed: The acidic activation domains of the baculovirus transactivators IE1 and IE0 are functional for transcriptional activation in both insect and mammalian cells. PubMed: Changes in cysteine protease activity and localization during midgut metamorphosis in the crucifer root maggot (Delia radicum). PubMed: Hemolymph ecdysteroids do not affect vitellogenesis in the lubber grasshopper. PubMed: Disagrees with AVMA's position on induced molting. PubMed: Phytoecdysteroids: biological effects, application in agriculture and complementary medicine (as presented at the 14-th Ecdysone Workshop, July, 2000, Rapperswil, Switzerland). PubMed: Effects of the ecdysoneless mutant on synaptic efficacy and structure at the neuromuscular junction in Drosophila larvae during normal and prolonged development. PubMed: Lethal and sublethal effects of bendiocarb, halofenozide, and imidacloprid on Harpalus pennsylvanicus (Coleoptera: Carabidae) following different modes of exposure in turfgrass. PubMed: Parallel alterations in the timing of ovarian ecdysone receptor and ultraspiracle expression characterize the independent evolution of larval reproduction in two species of gall midges (Diptera: Cecidomyiidae). PubMed: Biological activity of two juvenoids and two ecdysteroids against three stored product insects. PubMed: Cycling of ecdysteroid levels in adult female stable flies, Stomoxys calcitrans in relation to blood feeding. PubMed: Ecdysteroids during the third larval instar in 1(3)ecd-1ts, a temperature-sensitive mutant of Drosophila melanogaster. PubMed: Ecdysone-inducible functions of larval fat bodies in Drosophila. PubMed: Roles of ecdysone in Drosophila development. PubMed: Temporal relationships between leaving food, ecdysone release, mucoprotein extrusion and puparium formation in Drosophila virilis. PubMed: Dopa decarboxylase activity in Aedes aegypti: a preadult profile and its subsequent correlation with ovarian development. PubMed: The induction of detoxifying enzymes in insects. PubMed: Molt initiation in response to phytoecdysones and low doses of animal ecdysones in the chelicerate arthropod, Limulus polyphemus.