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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
Studies on the retention of plasmid DNA and Escherichia coli nucleic acids by hydrophobic interaction chromatography.
2001
[Purification of proteins in human plasma with new nylon affinity membranes].
2001 May
Development of cellulose-DNA immunoadsorbent.
2002 Feb
Hydrophobic interaction chromatography of homo-oligonucleotides on derivatized Sepharose CL-6B. Application of the solvophobic theory.
2002 Jan 25
Influence of the morphology of poly(EGDMA-co-HEMA) on the chemical modifications and retention of O-phosphothreonine.
2003 Jan 31
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
Immobilized protein ZZ, an affinity tool for immunoglobulin isolation and immunological experimentation.
2006 Sep
Affinity chromatography for the purification of therapeutic proteins from transgenic maize using immobilized histamine.
2008 Mar
Rapid determination of ractopamine residues in edible animal products by enzyme-linked immunosorbent assay: development and investigation of matrix effects.
2009
Review of soft tissue augmentation in the face.
2009 Aug 28
Development of 5-valent conjugate pneumococcal protein A - Capsular polysaccharide pneumococcal vaccine against invasive pneumococcal disease.
2009 Sep
Use of cross-linked carboxymethyl cellulose for soft-tissue augmentation: preliminary clinical studies.
2010 Nov 9
Platelet autologous growth factors decrease the osteochondral regeneration capability of a collagen-hydroxyapatite scaffold in a sheep model.
2010 Sep 27
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:43 UTC 2023
Edited
by admin
on Fri Dec 15 16:13:43 UTC 2023
Record UNII
E9MU425FIB
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID7024667
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
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SMS_ID
100000159555
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
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PUBCHEM
17046
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
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HSDB
5459
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
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NSC
24834
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
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CAS
2425-79-8
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
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FDA UNII
E9MU425FIB
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
ECHA (EC/EINECS)
219-371-7
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
PRIMARY
EVMPD
SUB169862
Created by admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
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