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| | DIPHENYLCYCLOPROPENONE Basic information |
| | 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) |
| Hazard Codes | Xi | | Risk Statements | 38-43 | | Safety Statements | 36/37 | | WGK Germany | 3 | | HS Code | 29142990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Skin Sens. 1 |
| | 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) (MBP1-10). 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 Preparation Products And Raw materials |
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