Diphenylcyclopropenone

• CAS: 886-38-4
• Catalog Number: ACM886384-1
• Category: Main Products
• Molecular Weight: 206.24
• Molecular Formula: C15H10O
• Synonyms: RARECHEM AQ C3 0050;1,2-DIPHENYLCYCLOPROPEN-3-ONE;2,3-DIPHENYL-2-CYCLOPROPEN-1-ONE;2,3-DIPHENYLCYCLOPROP-2-EN-1-ONE;Diphencyprone;DIPHENYLCYCLOPROPENONE;2,3-Diphenyl-2-cyclopropene-1-one;2,3-Diphenyl-cycloprop-2-enone
• IUPAC Name: 2,3-diphenylcycloprop-2-en-1-one
• Canonical SMILES: C1=CC=C(C=C1)C2=C(C2=O)C3=CC=CC=C3
• InChI Key: HCIBTBXNLVOFER-UHFFFAOYSA-N
• Boiling Point: 407.2ºC at 760 mmHg
• Melting Point: 118-122°C(lit.)
• Flash Point: 182.7ºC
• Density: 1.232
• Appearance: light red powder
• EC Number: 212-948-4
• Exact Mass: 206.07300
• Hazard Statements: Xi
• Safety Description: 36/37
• Supplemental Hazard Statements: H317
• Symbol: GHS07
• WGK Germany: 3

Case Study

Diphenylcyclopropenone for the Topical Immunotherapy of Alopecia Areata: A Randomized Clinical Trial of Combination versus Monotherapy

Ghandi N, et al. International Immunopharmacology, 2021, 99, 107971.

In a prospective randomized clinical trial, Diphenylcyclopropenone (DPCP), a well-established topical immunotherapeutic agent, was investigated for its efficacy in treating moderate to severe alopecia areata (AA), both as a monotherapy and in combination with anthralin. A total of 50 patients were randomly assigned into two groups: Group D received DPCP alone, while Group D/A was treated with DPCP in conjunction with topical anthralin. Treatment spanned a duration of six months, with the primary endpoint being the percentage of hair regrowth, and secondary outcomes including the frequency and severity of treatment-related adverse effects.
DPCP was applied weekly to sensitized scalp areas following a standard escalation protocol. In the combination group, anthralin was applied daily for 30-60 minutes before being washed off. Clinical response was assessed using standardized photographic evaluations and regrowth percentage scales. After 6 months, both groups showed comparable efficacy: complete hair regrowth occurred in 18.75% of Group D and 15.79% of Group D/A. Notably, >50% regrowth was observed in 47% of patients in the DPCP/anthralin group versus 31% in the DPCP-only group. However, these differences did not reach statistical significance (P = 0.696).
The study concluded that anthralin did not provide a synergistic benefit when combined with DPCP. Nevertheless, this research highlights the continued relevance of DPCP as a cornerstone in topical immunotherapy for alopecia areata.

Diphenylcyclopropenone for Multiple Bioconjugation via Selective Coupling with 1,2-Aminothiol

Liu S, et al.Chemical Communications, 2023, 59(11), 1497-1500.

Diphenylcyclopropenone (DPCP) has been demonstrated as a versatile reagent for site-selective bioconjugation, engaging in a unique reaction with 1,2-aminothiols in aqueous buffer (pH 7.4) to form amide linkages while releasing free thiol groups. This transformation, which proceeds under mild physiological conditions, enables modular and orthogonal protein labeling strategies. In the reported method, an N-terminal cysteine-containing peptide was treated with DPCP-Cl, a chlorinated analog of DPCP, to install the reactive DPCP moiety. Subsequent in situ thiol-maleimide coupling and tyrosine-diazonium labeling were performed sequentially in a single reaction vessel. This one-pot, triple-labelling strategy underscores the utility of DPCP in constructing multifunctional bioconjugates. Structural tuning of DPCP substituents allowed modulation of the coupling kinetics, with a Hammett reaction constant of +3.68, indicating strong electronic sensitivity. The reaction's chemoselectivity and aqueous compatibility make DPCP an efficient platform for developing advanced protein modification tools in chemical biology and therapeutic conjugate design.

Custom Q&A

What is the molecular formula of Diphenylcyclopropenone?

The molecular formula of Diphenylcyclopropenone is C15H10O.

What are the synonyms for Diphenylcyclopropenone?

The synonyms for Diphenylcyclopropenone are Diphencyprone and 2,3-Diphenylcycloprop-2-en-1-one.

What is the molecular weight of Diphenylcyclopropenone?

The molecular weight of Diphenylcyclopropenone is 206.24 g/mol.

What is the role of Diphenylcyclopropenone?

Diphenylcyclopropenone has a role as a photosensitizing agent, a hapten, and a drug allergen.

What has Diphenylcyclopropenone been used in trials for?

Diphenylcyclopropenone has been used in trials studying the treatment and basic science of Melanoma, Ultraviolet Rays, Immunosuppression, Neoplasm Metastasis, and Hypersensitivity, Delayed, among others.

What is the IUPAC name of Diphenylcyclopropenone?

The IUPAC name of Diphenylcyclopropenone is 2,3-diphenylcycloprop-2-en-1-one.

What is the InChI of Diphenylcyclopropenone?

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

What is the InChIKey of Diphenylcyclopropenone?

The InChIKey of Diphenylcyclopropenone is HCIBTBXNLVOFER-UHFFFAOYSA-N.

What is the CAS number of Diphenylcyclopropenone?

The CAS number of Diphenylcyclopropenone is 886-38-4.

What is the ChEMBL ID of Diphenylcyclopropenone?

The ChEMBL ID of Diphenylcyclopropenone is CHEMBL1373467.