DIPHENYLCYCLOPROPENONE Chemical Properties

Melting point:

118-122 °C (lit.)

Boiling point:

305.09°C (rough estimate)

Density 

1.232

refractive index 

1.6324 (estimate)

storage temp. 

Store below +30°C.

solubility 

DMF:20.0(Max Conc. mg/mL);96.97(Max Conc. mM)
DMSO:20.0(Max Conc. mg/mL);96.97(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);2.42(Max Conc. mM)
Ethanol:14.0(Max Conc. mg/mL);67.88(Max Conc. mM)

form 

Crystalline Powder

color 

Slightly pinkish-orange to beige

Merck 

14,3308

BRN 

608049

InChI

InChI=1S/C15H10O/c16-15-13(11-7-3-1-4-8-11)14(15)12-9-5-2-6-10-12/h1-10H

InChIKey

HCIBTBXNLVOFER-UHFFFAOYSA-N

SMILES

C1(=O)C(C2=CC=CC=C2)=C1C1=CC=CC=C1

LogP

1.769 (est)

CAS DataBase Reference

886-38-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

38-43

Safety Statements 

36/37

WGK Germany 

3

HS Code 

29142990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

DIPHENYLCYCLOPROPENONE Usage And Synthesis

Description

Diphencyprone (DCP) is a contact sensitizing agent. Pretreatment with DCP reduces symptom severity in a mouse model of experimental autoimmune encephalomyelitis (EAE) induced by myelin basic protein (1-10) (MBP_1-10). It enhances IL-10 production and antigen-specific IgG2a antibody responses and reduces anaphylaxis and asthma induced by ovalbumin in mice when administered during ovalbumin immunization at a concentration of 1% v/v. Topical administration of DCP increases intrafollicular CD4⁺ and CD8⁺ T cells, reduces upper dermal inflammation, and stimulates hair growth in the C3H/HeJ mouse model of alopecia areta. Formulations containing DCP have been used in the treatment of alopecia areta.

Description

Diphencyprone is a potent contact allergen responsible for occupational contact dermatitis in chemists and dermatological staff.

Chemical Properties

slightly pinkish-orange to beige crystalline

Uses

Diphenylcyclopropenone was used in topical immunotherapy.

Definition

ChEBI: A cyclopropenone compound having phenyl substituents at the 2- and 3-positions.

General Description

Diphenylcyclopropenone is a potent hapten. Its vibration frequency has been evaluated.

Contact allergens

Diphencyprone is a potent contact allergen used in topical immunotherapy to treat some severe alopecia areata. It is responsible for occupational contact dermatitis in chemists and dermatology department staff

Purification Methods

Crystallise it from cyclohexane. UV (MeCN): max 226, 282, 297nm. [Beilstein 17 IV 1736.]

References

[1] MICHAEL MEISTER . Self-Antigen Presentation by Keratinocytes in the Inflamed Adult Skin Modulates T-Cell Auto-Reactivity[J]. Journal of Investigative Dermatology, 2015, 135 8: Pages 1996-2004. DOI: 10.1038/jid.2015.130
[2] S. VON MOOS. The contact sensitizer diphenylcyclopropenone has adjuvant properties in mice and potential application in epicutaneous immunotherapy[J]. Allergy, 2012, 67 5: 638-646. DOI: 10.1111/j.1398-9995.2012.02802.x
[3] JOHN P. SUNDBERG . Alopecia Areata-Like Hair Loss in C3H/HeJ Mice and DEBR Rats Can be Reversed Using Topical Diphencyprone[J]. Journal of Investigative Dermatology Symposium Proceedings, 1999, 4 3: Page 239. DOI: 10.1038/sj.jidsp.5640219

DIPHENYLCYCLOPROPENONE(886-38-4)Related Product Information

• CIS-BETA-METHYLSTYRENE
• 2-Phenyl-1-propene
• β-Methylstyrene
• 2-Methyl-2-butene
• TRANS-2-METHYL-2-BUTENAL
• CIS-2-BUTENE
• 2-PHENYL-2-BUTENE
• α-Methylcinnamaldehyde
• 1,3-DIPHENYLPROPANE
• Methacrolein
• Cinnamaldehyde
• Phenylacetone
• 3-Pentanone
• 1,3-Diphenylacetone
• Phenylacetaldehyde
• 1-PHENYL-2-BUTANONE
• CIS-STILBENE
• DIPHENYLCYCLOPROPENONE