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Details

Stereochemistry MIXED
Molecular Formula C10H18O4
Molecular Weight 202.2475
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,4-BUTANEDIOL DIGLYCIDYL ETHER

SMILES

C(CCOCC1CO1)COCC2CO2

InChI

InChIKey=SHKUUQIDMUMQQK-UHFFFAOYSA-N
InChI=1S/C10H18O4/c1(3-11-5-9-7-13-9)2-4-12-6-10-8-14-10/h9-10H,1-8H2

HIDE SMILES / InChI
1,4-Butanediol diglycidyl ether (BDDE) is a viscous liquid, which is hygroscopic in nature. BDDE is the most commonly used homobifunctional epoxide compound. BDDE may react with amines, hydroxyls, sulfhydryl groups to produce secondary amines, ether or thioether bonds respectively. BDDE is a cross linking agent used • for preparing amylose, xylan and hydroxyethyl-cellulose • to cross link polyethylenimine which also serves as a hole-blocking layer in organic solar cells • to cross link hyaluronic acid (HA) into hydrogels • for the activation of soluble dextran polymers. • Amine or hydroxyl containing bis-epoxy supports are reacted with BDDE to form particles containing terminal epoxide group for immobilization reactions. In most commercial products, HA is crosslinked to increase its longevity, and the crosslinking agent used has an important effect on the properties of the final product; BDDE is the crosslinking agent used in the majority of the market-leading HA fillers, and its stability, biodegradability, and long safety record spanning more than 15 years are what make it the industry standard, ahead of other crosslinkers such as divinyl sulfone and 2,7,8-diepoxyoctane. Its ability to crosslink is attributed to the reactivity of the epoxide groups present at the two ends of the molecule. Under basic (pH > 7) conditions, these epoxide groups preferentially react with the most accessible primary alcohol in the HA backbone, forming an ether bond connection. The superior stability of the ether bond (relative to the ester or amide bond) is one of the reasons that BDDE-crosslinked HA fillers have a clinical duration that can reach or exceed 1 year. In addition, BDDE has a significantly lower toxicity than other ether-bond crosslinking chemistry based agents (e.g., divinyl sulfone), is biodegradable, and has been well studied.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Purification of proteins in human plasma with new nylon affinity membranes].
2001 May
Development of cellulose-DNA immunoadsorbent.
2002 Feb
Optimization of immobilized metal ion affinity chromatography for single-step purification of recombinant ovine growth hormone expressed in Escherichia coli.
2003 May 23
An attempt to improve diagnostics of contact allergy due to epoxy resin systems. First results of the multicentre study EPOX 2002.
2004 Nov-Dec
Contact vitiligo following a strong patch test reaction to triglycidyl-p-aminophenol in an aircraft industry worker: case report and review of the literature.
2005 Aug
Enzyme immunoassays for the analysis of streptomycin in milk, serum and water: development and assessment of a polyclonal antiserum and assay procedures using novel streptomycin derivatives.
2005 Jun
Backbone-thermoresponsive hyperbranched polyethers.
2006 Jun 28
Immobilized protein ZZ, an affinity tool for immunoglobulin isolation and immunological experimentation.
2006 Sep
Electrospun linear polyethyleneimine scaffolds for cell growth.
2007 Nov
Hyaluronic acid gel fillers in the management of facial aging.
2008
Rapid determination of ractopamine residues in edible animal products by enzyme-linked immunosorbent assay: development and investigation of matrix effects.
2009
Platelet autologous growth factors decrease the osteochondral regeneration capability of a collagen-hydroxyapatite scaffold in a sheep model.
2010 Sep 27
Patents
Name Type Language
1,4-BUTANEDIOL DIGLYCIDYL ETHER
Systematic Name English
BUTANEDIOL DIGLYCIDYL ETHER
Systematic Name English
1,4-BIS(2,3-EPOXYPROPOXY)BUTANE [HSDB]
Common Name English
ARALDIT DY 026
Brand Name English
BDDE
Common Name English
NSC-24834
Code English
1,4-BIS(2,3-EPOXYPROPOXY)BUTANE
HSDB  
Systematic Name English
OXIRANE, 2,2'-(1,4-BUTANEDIYLBIS(OXYMETHYLENE))BIS-
Systematic Name English
TK-10352
Code English
TK 10352
Code English
Code System Code Type Description
MESH
C014376
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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EPA CompTox
DTXSID7024667
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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SMS_ID
100000159555
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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PUBCHEM
17046
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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HSDB
5459
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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NSC
24834
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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CAS
2425-79-8
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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FDA UNII
E9MU425FIB
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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ECHA (EC/EINECS)
219-371-7
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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EVMPD
SUB169862
Created by admin on Fri Dec 15 16:13:43 GMT 2023 , Edited by admin on Fri Dec 15 16:13:43 GMT 2023
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