S-[11beta,17-dihydroxypregn-4-ene-3,20-dione] 21-(thiopivalate)

S-[11beta,17-dihydroxypregn-4-ene-3,20-dione] 21-(thiopivalate) Property

Melting point:

195-200°

alpha 

D20 +145° (c = 1 in dioxane)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Pale Yellow

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P321Specific treatment (see … on this label).

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

S-[11beta,17-dihydroxypregn-4-ene-3,20-dione] 21-(thiopivalate) Chemical Properties,Usage,Production

Chemical Properties

Pale Yellow Solid

Originator

Pivalone,Jouveinal,France,1978

Uses

Tixocortol 21-Pivalate is an anti-inflammatory agent. Tixocortol 21-Pivalate is used in fluorescent chemoaffinity labeling.

Uses

Anti-inflammatory. Used in fluorescent chemoaffinity labeling.

Uses

Free thiol in chemoaffinity labeling.

Definition

ChEBI: The pivalate thioester of tixocortol.

Manufacturing Process

In a reactor of 50 liters, sodium S-thiopivalate is prepared from 100 g of S_x0002_thiopivalic acid (0.844 mol), 214 cc of solution of sodium methylate, 3.95 M (0.844 mol) in 25 liters of anhydrous acetone.
There are then added 285 g (0.603 mol) of dihydroxy-11β,17α-iodo-21-dioxo- 3,20-pregnene-4 and the mixture is brought up to the acetone reflux for two hours. The solvent is eliminated by distillation under vacuum until there is obtained a syrupy residue which is poured into 10 liters of iced water. The insoluble part is filtered and dried under vacuum.
The crude product is purified by recrystallization from ethanol; weight: 250 g; yield: 89.5%.

Therapeutic Function

Antiinflammatory

Contact allergens

Tixocortol 21-pivalate is a 21-ester of tixocortol, widely used in topical treatments. It can induce severe allergic contact dermatitis. This corticosteroid is a marker of the allergenic A group that includes molecules without major substitution on the D cycle (no C 16 methylation, no C 17 side chain). A short-chain C 21 ester is possible. Molecules are cloprednol, cortisone, fludrocortisone, fluorometholone, hydrocortisone, methylprednisolone, methylprednisone, prednisolone, prednisone, tixocor- tol, and their C 21 esters (acetate, caproate or hexanoate, phosphate, pivalate or trimethylacetate, succinate or hemisuccinate, m-sulfobenzoate).