DHED

SIGMA/SML1642 - ≥98% (HPLC)

Synonym: (17β)-10,17-Dihydroxy-estra-1,4-dien-3-one; 10β,17β-Dihydroxyestra-1,4-dien-3-one; 3,16-Dihydroxyandrost-5-ene-17,19-dione

CAS Number: 549-02-0
Empirical Formula (Hill Notation): C₁₈H₂₄O₃
Molecular Weight: 288.38
Linear Formula: C₁₈H₂₄O₃
Product Type: Chemical

assay	≥98% (HPLC)
color	white to light brown
form	powder
InChI	1S/C18H24O3/c1-17-8-7-15-13(14(17)4-5-16(17)20)3-2-11-10-12(19)6-9-18(11,15)21/h6,9-10,13-16,20-21H,2-5,7-8H2,1H3/t13-,14-,15-,16-,17-,18+/m0/s1
InChI key	UIKDFTLKOKNUJP-UGDFAFBOSA-N
optical activity	[α]/D -20 to -30°, c = 1 in methanol
Quality Level	100
SMILES string	O[C@@]12C(CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@@H]4O)=CC(C=C1)=O
solubility	DMSO: 10 mg/mL, clear
storage temp.	2-8°C

Application:	DHED has been used to induce an increase of estrogen levels in 3K transgenic mice with Parkinson′s disease (PD)-like motor syndrome.
Biochem/physiol Actions:	DHED (10β,17β-dihydroxyestra-1,4-dien-3-one) is an inactive prodrug that selectively produces estrogen solely in the brain. DHED is converted to 17β-estradiol in the brain by an enzyme only expressed in the CNS, but is inert in the rest of the body. DHED was found to provide neuroprotection in a rat stroke model and reversed neurological symptoms of estrogen deprivation such as memory problems in female rats lacking ovaries.
Biochem/physiol Actions:	DHED is a substrate for nicotinamide adenine dinucleotide phosphate (NADPH)-dependent dehydrogenase/reductase. Its expression in the brain is correlated to neuroprotection functionality.
Biochem/physiol Actions:	DHED is an inactive prodrug that selectively produces estrogen solely in the brain.

Symbol	GHS08
Signal word	Danger
Hazard statements	H360Df
Precautionary statements	P201 - P280 - P308 + P313
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable