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
• Article Data: 4

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

Different sources of media describe the Uses of 13609-67-1 differently. You can refer to the following data:
1. antineoplastic
2. Hydrocortisone Butyrate is a topical corticosteroid use to treat a variety of dermatological conditions. It acts as an antiinflammatory, antiproliferative and immunosuppresive agent.
3. Hydrocortisone-17-butyrate is a topical corticosteroid with anti-inflammatory properties; marker for topical corticosteroid allergy.

Definition

ChEBI: Cortisol esterified with butyric acid at the 17-hydroxy group.

Brand name

Locoid (Ferndale); Locoid (Yamanouchi).

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

Downstream Products

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

Relevant articles and documents

An improved synthesis of corticosteroid 17α-esters by synthetic aluminium silicate-mediated conversion of 17α, 21-cyclic ortho esters

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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.