Dibutyl squarate

Dibutyl squarate
	source ↗
Names
	IUPAC name 3,4-Dibutoxy-3-cyclobutene-1,2-dione
	Other names Squaric acid dibutyl ester; SADBE
Identifiers
CAS Number	2892-62-8 Y;
3D model (JSmol)	Interactive image;
Beilstein Reference	1968189
ChEBI	CHEBI:53612;
ChEMBL	ChEMBL2435707;
ChemSpider	58618;
DrugBank	DB12223;
ECHA InfoCard	100.157.137
EC Number	628-906-7;
PubChem CID	65108;
UNII	4RTO57VG65;
CompTox Dashboard (EPA)	DTXSID30183113 ;
	InChI 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;
	SMILES CCCCOC1=C(C(=O)C1=O)OCCCC;
Properties
Chemical formula	C12H18O4
Molar mass	226.272 g·mol−1
Hazards
	GHS labelling:
Pictograms
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 [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 warts¹ and for treating alopecia areata or alopecia totalis (autoimmune hair loss) through topical immunotherapy involving the production of an allergic rash.²³ Dibutyl squarate is currently undergoing trials for use in treating herpes labialis (cold sores).⁴

References

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.
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.
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.
Kimball, Alexandra (5 May 2017), A Clinical Trial to Test the Safety and Efficacy of Squaric Acid Dibutyl Ester for the Treatment of Herpes Labialis, Massachusetts General Hospital

[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 (5 May 2017), A Clinical Trial to Test the Safety and Efficacy of Squaric Acid Dibutyl Ester for the Treatment of Herpes Labialis, Massachusetts General Hospital

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