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Dibutyl squarate

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Dibutyl squarate
Names
IUPAC name 3,4-Dibutoxy-3-cyclobutene-1,2-dione
Other names Squaric acid dibutyl ester; SADBE
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1968189
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.157.137 Edit this at Wikidata
EC Number
  • 628-906-7
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H18O4/c1-3-5-7-15-11-9(13)10(14)12(11)16-8-6-4-2/h3-8H2,1-2H3Key: XBRWELTXMQSEIN-UHFFFAOYSA-N
SMILES
  • CCCCOC1=C(C(=O)C1=O)OCCCC
Properties
Chemical formula C12H18O4
Molar mass 226.272 g·mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H317, H319, H335
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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 and for treating alopecia areata or alopecia totalis (autoimmune hair loss) through topical immunotherapy involving the production of an allergic rash. Dibutyl squarate is currently undergoing trials for use in treating herpes labialis (cold sores).

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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