Dibutyl squarate
Names
IUPAC name
3,4-Dibutoxy-3-cyclobutene-1,2-dione
Other names
Squaric acid dibutyl ester; SADBE
Identifiers
3D model (JSmol)
1968189
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.157.137
EC Number
  • 628-906-7
UNII
  • InChI=1S/C12H18O4/c1-3-5-7-15-11-9(13)10(14)12(11)16-8-6-4-2/h3-8H2,1-2H3
    Key: XBRWELTXMQSEIN-UHFFFAOYSA-N
  • CCCCOC1=C(C(=O)C1=O)OCCCC
Properties
C12H18O4
Molar mass 226.272 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H317, H319, H335
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P313, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dibutyl squarate (also known as squaric acid dibutyl ester or SADBE) is a chemical compound with the molecular formula C12H18O4. It is the dibutyl derivative of squaric acid.

Medically, it is used for the treatment of warts[1] and for treating alopecia areata or alopecia totalis (autoimmune hair loss) through topical immunotherapy involving the production of an allergic rash.[2][3] Dibutyl squarate is currently undergoing trials for use in treating herpes labialis (cold sores).[4]

References

  1. ↑ Silverberg, Nanette B.; Lim, Joseph K.; Paller, Amy S.; Mancini, Anthony J. (2000). "Squaric acid immunotherapy for warts in children". Journal of the American Academy of Dermatology. 42 (5): 803–808. doi:10.1067/mjd.2000.103631. PMID 10775858.
  2. ↑ Yoshimasu, Takashi; Furukawa, Fukumi (2016). "Modified immunotherapy for alopecia areata". Autoimmunity Reviews. 15 (7): 664–667. doi:10.1016/j.autrev.2016.02.021. PMID 26932732.
  3. ↑ Holzer, A. M.; Kaplan, L. L.; Levis, W. R. (2006). "Haptens as drugs: contact allergens are powerful topical immunomodulators". J. Drugs Dermatol. 5 (5): 410–416. PMID 16703776.
  4. ↑ Kimball, Alexandra (2017-05-05). "A Clinical Trial to Test the Safety and Efficacy of Squaric Acid Dibutyl Ester for the Treatment of Herpes Labialis". Massachusetts General Hospital. {{cite journal}}: Cite journal requires |journal= (help)
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