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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

Molecular Formula C10H18O4
Molecular Weight 202.2475
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Use of cross-linked carboxymethyl cellulose for soft-tissue augmentation: preliminary clinical studies.
2010-11-09
Platelet autologous growth factors decrease the osteochondral regeneration capability of a collagen-hydroxyapatite scaffold in a sheep model.
2010-09-27
Development of 5-valent conjugate pneumococcal protein A - Capsular polysaccharide pneumococcal vaccine against invasive pneumococcal disease.
2009-09
Review of soft tissue augmentation in the face.
2009-08-28
Rapid determination of ractopamine residues in edible animal products by enzyme-linked immunosorbent assay: development and investigation of matrix effects.
2009
New developments in the preparation of anion exchange media based on hyperbranched condensation polymers.
2008-12-05
Affinity chromatography for the purification of therapeutic proteins from transgenic maize using immobilized histamine.
2008-03
Hyaluronic acid gel (Juvéderm) preparations in the treatment of facial wrinkles and folds.
2008
Hyaluronic acid gel fillers in the management of facial aging.
2008
Electrospun linear polyethyleneimine scaffolds for cell growth.
2007-11
Open tubular anion exchange chromatography. Controlled layered architecture of stationary phase by successive condensation polymerization.
2007-07-15
Immobilized protein ZZ, an affinity tool for immunoglobulin isolation and immunological experimentation.
2006-09
Backbone-thermoresponsive hyperbranched polyethers.
2006-06-28
Immobilized metal affinity chromatography of monoclonal immunoglobulin M against mutant amidase from Pseudomonas aeruginosa.
2006-06
Contact vitiligo following a strong patch test reaction to triglycidyl-p-aminophenol in an aircraft industry worker: case report and review of the literature.
2005-08
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.
2005-06
An attempt to improve diagnostics of contact allergy due to epoxy resin systems. First results of the multicentre study EPOX 2002.
2004-12-21
Immobilized cofactor derivatives for kinetic-based enzyme capture strategies: direct coupling of NAD(P)+.
2004-12-15
Development of a plate technique for screening of polysaccharide-degrading microorganisms by using a mixture of insoluble chromogenic substrates.
2004-03
Optimization of immobilized metal ion affinity chromatography for single-step purification of recombinant ovine growth hormone expressed in Escherichia coli.
2003-05-23
Influence of the morphology of poly(EGDMA-co-HEMA) on the chemical modifications and retention of O-phosphothreonine.
2003-01-31
Development of cellulose-DNA immunoadsorbent.
2002-02
Hydrophobic interaction chromatography of homo-oligonucleotides on derivatized Sepharose CL-6B. Application of the solvophobic theory.
2002-01-25
[Purification of proteins in human plasma with new nylon affinity membranes].
2001-05
Studies on the retention of plasmid DNA and Escherichia coli nucleic acids by hydrophobic interaction chromatography.
2001
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:22:29 GMT 2025
Edited
by admin
on Mon Mar 31 18:22:29 GMT 2025
Record UNII
E9MU425FIB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,4-BIS(2,3-EPOXYPROPOXY)BUTANE
HSDB  
Preferred Name English
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
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 Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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EPA CompTox
DTXSID7024667
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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SMS_ID
100000159555
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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PUBCHEM
17046
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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HSDB
5459
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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NSC
24834
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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CAS
2425-79-8
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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FDA UNII
E9MU425FIB
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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ECHA (EC/EINECS)
219-371-7
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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EVMPD
SUB169862
Created by admin on Mon Mar 31 18:22:29 GMT 2025 , Edited by admin on Mon Mar 31 18:22:29 GMT 2025
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