13609-67-1

Basic information

• Product Name: Hydrocortisone-17-butyrate
• Synonyms: locoid;Hydrocortisone Butyrate USP;Pregn-4-ene-3,20-dione, 11,21-dihydroxy-17-(1-oxobutoxy)-, (11.beta.)-;11β,17,21-trihydroxypregn-4-ene-3,20-dione 17-butyrate;4-Pregnene-11β,21-dihydroxy-17α-butyryloxy-3,20-dione;Alfason;Butyric acid, 17-ester with cortisol (8CI);Cortisol, 17-butyrate (6CI, 8CI)
• CAS NO: 13609-67-1
• Molecular Formula: C₂₅H₃₆O₆
• Molecular Weight: 432.55
• EINECS: 237-093-4
• Product Categories: Steroids;Steroid and Hormone;NOVANTRONE
• Mol File: 13609-67-1.mol

Chemical Properties

• Melting Point: 210.0 to 214.0 °C
• Boiling Point: 466.2°C (rough estimate)
• Flash Point: 194 °C
• Appearance: /
• Density: 1.0914 (rough estimate)
• Vapor Pressure: 3.76E-16mmHg at 25°C
• Refractive Index: 1.4593 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.98±0.10(Predicted)
• Merck: 14,4787
• CAS DataBase Reference: Hydrocortisone-17-butyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Hydrocortisone-17-butyrate(13609-67-1)
• EPA Substance Registry System: Hydrocortisone-17-butyrate(13609-67-1)

Safety Data

• WGK Germany: 2
• RTECS: GM9002000
• Hazardous Substances Data: 13609-67-1(Hazardous Substances Data)

Usage

Uses

Used in Dermatology:
Hydrocortisone-17-butyrate is used as a topical corticosteroid for the treatment of various dermatological conditions. It acts as an anti-inflammatory, antiproliferative, and immunosuppressive agent, helping to alleviate inflammation, reduce the risk of skin cell overgrowth, and suppress the immune response in the affected area.
Used in Allergy Testing:
Hydrocortisone-17-butyrate is used as a marker for topical corticosteroid allergy. This application aids in identifying individuals who may have an allergic reaction to corticosteroids, which is crucial for determining the appropriate treatment options for their dermatological conditions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Hydrocortisone-17-butyrate is used as an active ingredient in various topical formulations, such as creams, ointments, and lotions. These formulations are designed to provide targeted relief for skin conditions like eczema, psoriasis, and contact dermatitis.
Brand Names:
Some of the brand names under which Hydrocortisone-17-butyrate is marketed include Locoid (Ferndale) and Locoid (Yamanouchi). These products are widely recognized and trusted for their effectiveness in managing various skin conditions.

Biochem/physiol Actions

Hydrocortisone 17-butyrate is a corticosteroid that acts as a dermocorticoid due to its application in dermatological therapy. It exhibits therapeutic effects against vitiligo of the face and neck.

Contact allergens

Hydrocortisone 17-butyrate is a C 17 ester of hydrocorti- sone. It represents the D2 group of corticosteroids, non C 16 methylated with a C 17 ester: hydrocortisone 17-butyrate, hydrocortisone 17-valerate, hydrocortisone aceponate (17-propionate and 21-acetate), methylpred- nisolone aceponate, and prednicarbate. It is sometimes hydrolyzed in vivo into hydrocortisone, giving allergic reactions to group-A-sensitized people.

InChI:InChI=1/C25H36O6/c1-4-5-21(30)31-25(20(29)14-26)11-9-18-17-7-6-15-12-16(27)8-10-23(15,2)22(17)19(28)13-24(18,25)3/h12,17-19,22,26,28H,4-11,13-14H2,1-3H3/t17-,18?,19-,22?,23-,24-,25-/m0/s1

Synthetic route

Hydrocortisone 17α,21-ethyl orthobutanoate (49757-02-0) → hydrocortisone 17α-butyrate (13609-67-1)

Conditions	Yield
aluminium silicate In methanol; water for 1h; Heating;	78%

HYDROCORTISONE (50-23-7) + 1,1,1-trimethoxybutane (43083-12-1) → hydrocortisone 17α-butyrate (13609-67-1) + 21-oxobutoxy-11β,17α-dihydroxypregn-4-ene-3,20-dione (6677-99-2)

Conditions	Yield
With hydrogenchloride; toluene-4-sulfonic acid 1) acetonitrile, 13 min, 2) acetonitrile, 14 min; Yield given. Multistep reaction. Yields of byproduct given;

HYDROCORTISONE (50-23-7) → hydrocortisone 17α-butyrate (13609-67-1)

Conditions	Yield
In methanol; aqueous oxalic acid

hydrocortisone 17α-butyrate (13609-67-1) → 21-dehydrohydrocortisone-17-butyrate

Conditions	Yield
With air; copper diacetate In ethanol for 5h;	100%
copper diacetate In methanol
copper diacetate In methanol

propylsulfanyl-acetyl chloride (55016-23-4) + hydrocortisone 17α-butyrate (13609-67-1) → 17α-Butanoyloxy-11β-hydroxy-21-(propylthio)acetoxy-4-pregnene-3,20-dione (121507-14-0)

Conditions	Yield
With pyridine In chloroform ice-cooling;	78%

2-(ethylthio)acetyl chloride (54256-37-0) + hydrocortisone 17α-butyrate (13609-67-1) → 17α-Butanoyloxy-21-(ethylthio)acetoxy-11β-hydroxy-4-pregnene-3,20-dione (121507-13-9)

Conditions	Yield
With pyridine In chloroform ice-cooling;	49%

hydrocortisone 17α-butyrate (13609-67-1) + (aminooxy)acetic acid hemihydrochloride (2921-14-4, 7776-18-3, 20295-82-3) → anti-cortisol 17-butyrate-3-(O-carboxymethyl)-oxime + syn-cortisol 17-butyrate-3-(O-carboxymethyl)-oxime

Conditions	Yield
With sodium acetate In 1,4-dioxane; methanol; water	A 48% B 25%

(methylthio)acetyl chloride (35928-65-5) + hydrocortisone 17α-butyrate (13609-67-1) → 17α-Butanoyloxy-11β-hydroxy-21-(methylthio)acetoxy-4-pregnene-3,20-dione (121507-12-8)

Conditions	Yield
With pyridine In chloroform for 0.666667h;	33%

hydrocortisone 17α-butyrate (13609-67-1) + dimethyl sulfoxide (67-68-5) → 17α-Butanoyloxy-11β-hydroxy-21-(methylthio)methoxy-4-pregnene-3,20-dione (128557-21-1)

Conditions	Yield
With acetic anhydride; acetic acid In acetonitrile Heating;	18%

hydrocortisone 17α-butyrate (13609-67-1) → 21-oxobutoxy-11β,17α-dihydroxypregn-4-ene-3,20-dione (6677-99-2)

Conditions	Yield
With propylene glycol at 60℃; Rate constant;
In ethanol at 60℃; for 72h; Yield given;

benzene-n-hexane + hydrocortisone 17α-butyrate (13609-67-1) → hydrocortisone butyrate propionate (72590-77-3)

Conditions	Yield
In pyridine; ethanol; water

hydrocortisone 17α-butyrate (13609-67-1) → HYDROCORTISONE (50-23-7)

Conditions	Yield
With potassium hydroxide In methanol; dichloromethane at -5 - 0℃; for 1.5h; Temperature; Reagent/catalyst; Inert atmosphere;	60.3 g

Upstream product

• 50-23-7 HYDROCORTISONE 
• 43083-12-1 1,1,1-trimethoxybutane 
• 49757-02-0 Hydrocortisone 17α,21-ethyl orthobutanoate 

Downstream Products

• 72590-77-3 hydrocortisone butyrate propionate 
• 50-23-7 HYDROCORTISONE 
• 6677-99-2 21-oxobutoxy-11β,17α-dihydroxypregn-4-ene-3,20-dione 

Relevant articles and documents

Composition for the topical treatment of poison ivy and other forms of contact dermatitis

Composition for topical administration comprising (a) a corticosteroid, and (b) a drying agent.

Novel hydrocortisone derivative

17α-butyryloxy-11β-hydroxy-21-propionyloxy-4-pregnen-3,20-dione, i.e., hydrocortisone 17-butyrate 21-propionate of the present invention is prepared by acylating hydrocortisone 17-butyrate with propionic acid anhydride or halide. The compound of the present invention has excellent anti-inflammatory effect, percutaneous absorption and less side effect.