Pregnandiol

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Structural formula
Structural formula of pregnanediol
General
Surname Pregnandiol
other names

(3 α , 5 β , 20 α ) -Pregnan-3,20-diol

Molecular formula C 21 H 36 O 2
External identifiers / databases
CAS number 80-92-2
EC number 201-313-7
ECHA InfoCard 100.001.195
PubChem 4901
Wikidata Q906054
properties
Molar mass 320.51 g mol −1
Physical state

firmly

Melting point

243.5 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: ?
Toxicological data

7 mg kg −1 ( LD Lo ,  mouse ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pregnandiol is a hormonally ineffective breakdown product of progesterone and other progesterone-related gestagens , which all belong to the group of female sex hormones .

discovery

From the urine of pregnant women from London clinics, Guy Frederic Marrian isolated a substance that contained two hydroxyl groups and which could be converted into a diacetate with acetic anhydride . However, the formula was not clearly established. Almost at the same time, Adolf Butenandt examined the components of the urine of pregnant women in the Göttingen University Chemical Laboratory and clarified the structure of the diol . The name Pregnandiol coined by Butenandt is derived from the Latin verb praegnans (pregnant, pregnant), or the English pregnant and Pregnancy (pregnancy). This gave rise to the name Pregnan for the underlying parent hydrocarbon.

biogenesis

Progesterone is largely converted (metabolized) in the liver to pregnanediol, and after it has been esterified to pregnanediol glucoronide with the help of glucuronic acid , it is excreted in the urine . Therefore, conclusions can be drawn from an increased pregnanediol glucoronide level in the urine about an increased progesterone level, which is usually associated with pregnancy .

swell

  1. ↑ a b Entry on pregnanediol in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on January 20, 2020.
  2. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 5-β-pregnane-3-α, 20-α-diol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 20, 2020, is reproduced from a self-classification by the distributor .
  3. ↑ Guy Frederic Marrian, Biochemical Journal 1929, Vol. 23, Issue 5, pp. 1090-1098.
  4. ↑ Adolf Butenandt: About the Pregnandiol, a new sterol derivative from pregnant woman's urine , reports of the German Chemical Society, 1930, vol. 63, p. 659

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