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3073-59-4,MFCD00008684
Catalog No.:AA0030ZQ

3073-59-4 | N,N'-(Hexane-1,6-diyl)diacetamide

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25g
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50g
≥95%
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250g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0030ZQ
Chemical Name:
N,N'-(Hexane-1,6-diyl)diacetamide
CAS Number:
3073-59-4
Molecular Formula:
C10H20N2O2
Molecular Weight:
200.2780
MDL Number:
MFCD00008684
SMILES:
CC(=O)NCCCCCCNC(=O)C
NSC Number:
95580
Properties
Properties
 
BP:
456.7°C at 760 mmHg  
Form:
Solid  
MP:
128-129℃(lit.)  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
161  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
7  
XLogP3:
0.3  

Downstream Synthesis Route

[1]ChemischeBerichte,1959,vol.92,p.970,975

[1]JournalfurpraktischeChemie(Leipzig1954),vol.62,p.210

[1]JournalofOrganicChemistry,1955,vol.20,p.695,697

3073-59-4   
C10H19Cl2IN2O2 

[1]Sovietprogressinchemistry,1977,vol.43,p.44-46    UkrainskiiKhimicheskiiZhurnal(RussianEdition),1977,vol.43,p.384-387

[1]Chemicalandpharmaceuticalbulletin,1978,vol.26,p.2422-2427

Literature

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Journal: The Journal of biological chemistry 20160722

Title: Cancer Differentiating Agent Hexamethylene Bisacetamide Inhibits BET Bromodomain Proteins.

Journal: Cancer research 20160415

Title: Bromodomain and extra-terminal (BET) bromodomain inhibition activate transcription via transient release of positive transcription elongation factor b (P-TEFb) from 7SK small nuclear ribonucleoprotein.

Journal: The Journal of biological chemistry 20121019

Title: Entry of herpes simplex virus type 1 (HSV-1) into the distal axons of trigeminal neurons favors the onset of nonproductive, silent infection.

Journal: PLoS pathogens 20120501

Title: Bis-pyrrolyl-tetrazolyl derivatives as hybrid polar compounds: A case of lipophilic functional bioisosterism with bis-acetamides.

Journal: European journal of medicinal chemistry 20120401

Title: Transient reversal of episome silencing precedes VP16-dependent transcription during reactivation of latent HSV-1 in neurons.

Journal: PLoS pathogens 20120201

Title: 7SK snRNA: a noncoding RNA that plays a major role in regulating eukaryotic transcription.

Journal: Wiley interdisciplinary reviews. RNA 20120101

Title: A flexible model of HIV-1 latency permitting evaluation of many primary CD4 T-cell reservoirs.

Journal: PloS one 20120101

Title: DNA replication fading as proliferating cells advance in their commitment to terminal differentiation.

Journal: Scientific reports 20120101

Title: Vorinostat approved in Japan for treatment of cutaneous T-cell lymphomas: status and prospects.

Journal: OncoTargets and therapy 20120101

Title: Potentiation of NMDA receptor-dependent cell responses by extracellular high mobility group box 1 protein.

Journal: PloS one 20120101

Title: Distribution and shedding of the membrane phosphatidylserine during maturation and aging of erythroid cells.

Journal: Biochimica et biophysica acta 20111201

Title: Cholesterol esterification during differentiation of mouse erythroleukemia (Friend) cells.

Journal: Hematology reports 20110831

Title: Determination of hexamethylene bisacetamide, an antineoplastic compound, in mouse and human plasma by LC-MS/MS.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110801

Title: NPMc(+) AML cell line shows differential protein expression and lower sensitivity to DNA-damaging and p53-inducing anticancer compounds.

Journal: Cell cycle (Georgetown, Tex.) 20110615

Title: New insights into the control of HIV-1 transcription: when Tat meets the 7SK snRNP and super elongation complex (SEC).

Journal: Journal of neuroimmune pharmacology : the official journal of the Society on NeuroImmune Pharmacology 20110601

Title: Aberrant expression and localization of hnRNP-A2/B1 is a common event in human gastric adenocarcinoma.

Journal: Journal of gastroenterology and hepatology 20110101

Title: Mouse embryonic stem cells inhibit murine cytomegalovirus infection through a multi-step process.

Journal: PloS one 20110101

Title: P27(Kip1), regulated by glycogen synthase kinase-3β, results in HMBA-induced differentiation of human gastric cancer cells.

Journal: BMC cancer 20110101

Title: Somatic mutagenesis with a Sleeping Beauty transposon system leads to solid tumor formation in zebrafish.

Journal: PloS one 20110101

Title: Protein phosphatase-1 activates CDK9 by dephosphorylating Ser175.

Journal: PloS one 20110101

Title: DMSO-Free Programmed Cryopreservation of Fully Dissociated and Adherent Human Induced Pluripotent Stem Cells.

Journal: Stem cells international 20110101

Title: Expression of prion protein in mouse erythroid progenitors and differentiating murine erythroleukemia cells.

Journal: PloS one 20110101

Title: Antivirals reduce the formation of key Alzheimer's disease molecules in cell cultures acutely infected with herpes simplex virus type 1.

Journal: PloS one 20110101

Title: Localization and altered expression of nucleophosmin in the nuclear matrix during the differentiation of human hepatocarcinoma SMMC-7721 cells induced by HMBA.

Journal: Cancer investigation 20101201

Title: Antagonistic roles of the ERK and p38 MAPK signalling pathways in globin expression, haem biosynthesis and iron uptake.

Journal: The Biochemical journal 20101115

Title: Occupational exposure to HDI: progress and challenges in biomarker analysis.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20101001

Title: Sequential changes in chromatin structure during transcriptional activation in the beta globin LCR and its target gene.

Journal: The international journal of biochemistry & cell biology 20100901

Title: HMBA depolymerizes microtubules, activates mitotic checkpoints and induces mitotic block in MCF-7 cells by binding at the colchicine site in tubulin.

Journal: Biochemical pharmacology 20100701

Title: Aberrant expression of nuclear matrix proteins during HMBA-induced differentiation of gastric cancer cells.

Journal: World journal of gastroenterology 20100507

Title: Constitutive and Inducible Innate Responses in Cells Infected by HSV-1-Derived Amplicon Vectors.

Journal: The open virology journal 20100101

Title: Interferon alpha induces establishment of alphaherpesvirus latency in sensory neurons in vitro.

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Title: Hepcidin induces HIV-1 transcription inhibited by ferroportin.

Journal: Retrovirology 20100101

Title: Content-based microarray search using differential expression profiles.

Journal: BMC bioinformatics 20100101

Title: De novo synthesis of VP16 coordinates the exit from HSV latency in vivo.

Journal: PLoS pathogens 20090301

Title: Hexamethylene bisacetamide can convert nonpermissive human cells to a permissive state for expressing the major immediate-early genes of human cytomegalovirus by up-regulating NF-kappaB activity.

Journal: Virology 20090120

Title: Control of stochastic gene expression by host factors at the HIV promoter.

Journal: PLoS pathogens 20090101

Title: Gene therapy: the end of the rainbow?

Journal: Head & neck oncology 20090101

Title: Properties of virion transactivator proteins encoded by primate cytomegaloviruses.

Journal: Virology journal 20090101

Title: P-TEFb- the final frontier.

Journal: Cell division 20090101

Title: Wnt pathway reprogramming during human embryonal carcinoma differentiation and potential for therapeutic targeting.

Journal: BMC cancer 20090101

Title: Molecular control of HIV-1 postintegration latency: implications for the development of new therapeutic strategies.

Journal: Retrovirology 20090101

Title: A potential novel combination therapy targeting survivin in renal cancer cells: Inhibition of survivin expression by topotecan and hexamethylene bisacetamide.

Journal: Molecular medicine reports 20090101

Title: Discordant varicella-zoster virus glycoprotein C expression and localization between cultured cells and human skin vesicles.

Journal: Virology 20081220

Title: Hexamethylene bisacetamide (HMBA) simultaneously targets AKT and MAPK pathway and represses NF kappaB activity: implications for cancer therapy.

Journal: Cell cycle (Georgetown, Tex.) 20081201

Title: [Molecular mechanism underlying differentiation of HL-60 cells induced by hexamethylene bisacetamide].

Journal: Zhongguo shi yan xue ye xue za zhi 20081001

Title: HEXIM1 regulates 17beta-estradiol/estrogen receptor-alpha-mediated expression of cyclin D1 in mammary cells via modulation of P-TEFb.

Journal: Cancer research 20080901

Title: [Expression and localization of hnRNP A2/B1 during differentiation of human osteosarcoma MG-63 cells induced by HMBA].

Journal: Ai zheng = Aizheng = Chinese journal of cancer 20080701

Title: PP2B and PP1alpha cooperatively disrupt 7SK snRNP to release P-TEFb for transcription in response to Ca2+ signaling.

Journal: Genes & development 20080515

Title: Hexamethylene bisacetamide inhibits malignant phenotype in T-ALL cell lines.

Journal: Leukemia research 20080501

Title: Hexamethylene bisacetamide as a treatment for T-cell leukemia (T-ALL).

Journal: Leukemia research 20080501

Title: Non-random subcellular distribution of variant EKLF in erythroid cells.

Journal: Experimental cell research 20080415

Title: Hexamethylbisacetamide and disruption of human immunodeficiency virus type 1 latency in CD4(+) T cells.

Journal: The Journal of infectious diseases 20080415

Title: Effect of hexamethylene bisacetamide (HMBA) on the microtubular system of Tetrahymena pyriformis.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20080201

Title: Hexamethylene bisacetamide leads to reduced helper virus-free HSV-1 amplicon expression titers via suppression of ICP0.

Journal: The journal of gene medicine 20080201

Title: [Localization of prohibitin in nuclear matrix and its expressive alteration during the differentiation of human osteosarcoma MG-63 cells induced by HMBA].

Journal: Fen zi xi bao sheng wu xue bao = Journal of molecular cell biology 20080201

Title: PU.1 is dispensable to block erythroid differentiation in Friend erythroleukemia cells.

Journal: Leukemia research 20080101

Title: Relationship between the induction of leukemia cell differentiation and the enhancement of reporter gene expression in 3T3 Swiss cells.

Journal: Leukemia research 20080101

Title: Histone modifications associated with herpes simplex virus type 1 genomes during quiescence and following ICP0-mediated de-repression.

Journal: The Journal of general virology 20080101

Title: Overexpression of CDC2/CyclinB1 in gliomas, and CDC2 depletion inhibits proliferation of human glioma cells in vitro and in vivo.

Journal: BMC cancer 20080101

Title: Detailed characterization of the mouse embryonic stem cell transcriptome reveals novel genes and intergenic splicing associated with pluripotency.

Journal: BMC genomics 20080101

Title: Multi-stage Friend murine erythroleukemia: molecular insights into oncogenic cooperation.

Journal: Retrovirology 20080101

Title: Defeating cancer with antidepressants.

Journal: Ecancermedicalscience 20080101

Title: HMBA releases P-TEFb from HEXIM1 and 7SK snRNA via PI3K/Akt and activates HIV transcription.

Journal: PLoS pathogens 20071001

Title: HEXIM1 and the control of transcription elongation: from cancer and inflammation to AIDS and cardiac hypertrophy.

Journal: Cell cycle (Georgetown, Tex.) 20070801

Title: Alteration of nuclear matrix-intermediate filament system and differential expression of nuclear matrix proteins during human hepatocarcinoma cell differentiation.

Journal: World journal of gastroenterology 20070528

Title: Proteomic analysis of erythroid differentiation induced by hexamethylene bisacetamide in murine erythroleukemia cells.

Journal: Experimental hematology 20070201

Title: Down-regulation of CD44 contributes to the differentiation of HL-60 cells induced by ATRA or HMBA.

Journal: Cellular & molecular immunology 20070201

Title: Temporal variation in the expression of the p53 protein in proliferating and differentiating murine erythroleukaemia cells.

Journal: Molecular and cellular biochemistry 20070101

Title: Cellular mRNA activates transcription elongation by displacing 7SK RNA.

Journal: PloS one 20070101

Title: Delayed biosynthesis of varicella-zoster virus glycoprotein C: upregulation by hexamethylene bisacetamide and retinoic acid treatment of infected cells.

Journal: Journal of virology 20061001

Title: Enhancement of antitumor activity of herpes simplex virus gamma(1)34.5-deficient mutant for oral squamous cell carcinoma cells by hexamethylene bisacetamide.

Journal: Cancer gene therapy 20060801

Title: Growth inhibition and differentiation of human breast cancer cells by the PAFR antagonist WEB-2086.

Journal: British journal of cancer 20060605

Title: The carbonic anhydrase I locus contains a c-Myb target promoter and modulates differentiation of murine erythroleukemia cells.

Journal: Oncogene 20060504

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Following the differentiation of human pluripotent stem cells by proteomic identification of biomarkers.

Journal: Stem cells and development 20060401

Title: [Changes of nuclear matrix proteins during differentiation of human osteosarcoma MG-63 cells induced by HMBA].

Journal: Fen zi xi bao sheng wu xue bao = Journal of molecular cell biology 20060401

Title: Increased HEXIM1 expression during erythroleukemia and neuroblastoma cell differentiation.

Journal: Journal of cellular physiology 20060301

Title: 1,6-Diaminohexane contributes to the hexamethylene bisacetamide-induced erythroid differentiation pathway by stimulating Ca2+ release from inositol 1,4,5-trisphosphate-sensitive stores and promoting Ca2+ influx.

Journal: Archives of biochemistry and biophysics 20060101

Title: Differentiation-inducing therapy for solid tumors.

Journal: Current pharmaceutical design 20060101

Title: Changes of nuclear matrix proteins following the differentiation of human osteosarcoma MG-63 cells.

Journal: Genomics, proteomics & bioinformatics 20060101

Title: Interplay between 7SK snRNA and oppositely charged regions in HEXIM1 direct the inhibition of P-TEFb.

Journal: The EMBO journal 20051221

Title: Inhibitory effect of hexamethylene bisacetamide on replication of human cytomegalovirus.

Journal: Archives of virology 20051001

Title: Microarray profiling of genes differentially expressed during erythroid differentiation of murine erythroleukemia cells.

Journal: Molecules and cells 20050831

Title: Protein kinase clk/STY is differentially regulated during erythroleukemia cell differentiation: a bias toward the skipped splice variant characterizes postcommitment stages.

Journal: Cell research 20050701

Title: Temporal changes in the expression of protein phosphatase 1 and protein phosphatase 2A in proliferating and differentiating murine erythroleukaemia cells.

Journal: Cell biology international 20050401

Title: A new paradigm in eukaryotic biology: HIV Tat and the control of transcriptional elongation.

Journal: PLoS biology 20050201

Title: Histone H4 hyperacetylation precludes histone H4 lysine 20 trimethylation.

Journal: The Journal of biological chemistry 20041217

Title: HMBA induces cell death and potentiates doxorubicin toxicity in malignant mesothelioma cells.

Journal: Cancer chemotherapy and pharmacology 20041101

Title: Applying proteomic methodologies to analyze the effect of hexamethylene bisacetamide (HMBA) on proliferation and differentiation of human gastric carcinoma BGC-823 cells.

Journal: The international journal of biochemistry & cell biology 20040801

Title: Activation of transiently transfected reporter genes in 3T3 Swiss cells by the inducers of differentiation/apoptosis--dimethylsulfoxide, hexamethylene bisacetamide and trichostatin A.

Journal: European journal of biochemistry 20040601

Title: Differentiation-dependent photodynamic therapy regulated by porphobilinogen deaminase in B16 melanoma.

Journal: British journal of cancer 20040504

Title: Growth arrest and apoptosis of human hepatocellular carcinoma cells induced by hexamethylene bisacetamide.

Journal: World journal of gastroenterology 20040401

Title: HMBA-induced differentiation of myeloid leukemic cell lines is associated with altered G1 cell cycle regulators and related genes.

Journal: Chinese medical journal 20040301

Title: [Effect of HMBA on differentiation and apoptosis of HL-60 and U937 cells and its mechanism].

Journal: Zhonghua xue ye xue za zhi = Zhonghua xueyexue zazhi 20040301

Title: Altered interaction of HDAC5 with GATA-1 during MEL cell differentiation.

Journal: Oncogene 20031211

Title: Overexpression of the immediate early gene fra-1 inhibits proliferation, induces apoptosis, and reduces tumourigenicity of c6 glioma cells.

Journal: Experimental cell research 20031115

Title: [Effects of hexamethylene bisacetamide on cell cycle and expression of its regulatory proteins in HL-60 cells].

Journal: Zhongguo shi yan xue ye xue za zhi 20031001

Title: Inhibition of P-TEFb (CDK9/Cyclin T) kinase and RNA polymerase II transcription by the coordinated actions of HEXIM1 and 7SK snRNA.

Journal: Molecular cell 20031001

Title: Identification of a novel inhibitor of breast cell growth that is down-regulated by estrogens and decreased in breast tumors.

Journal: Cancer research 20030815

Title: A porphobilinogen deaminase (PBGD) Ran-binding protein interaction is implicated in nuclear trafficking of PBGD in differentiating glioma cells.

Journal: Oncogene 20030814

Title: Differential expression of Ran GTPase during HMBA-induced differentiation in murine erythroleukemia cells.

Journal: Leukemia research 20030701

Title: The cleavage product deltaPML-RARalpha contributes to all-trans retinoic acid-mediated differentiation in acute promyelocytic leukemia cells.

Journal: Oncogene 20030626

Title: Modulation of SOX2 and SOX3 gene expression during differentiation of human neuronal precursor cell line NTERA2.

Journal: Molecular biology reports 20030601

Title: Clinical and laboratory studies of expression of cyclin A in leukemia cells.

Journal: Zhongguo shi yan xue ye xue za zhi 20030401

Title: Suppression of NF-kappaB-dependent gene expression by a hexamethylene bisacetamide-inducible protein HEXIM1 in human vascular smooth muscle cells.

Journal: Genes to cells : devoted to molecular & cellular mechanisms 20030201

Title: Leukemia-related transcription factor TEL accelerates differentiation of Friend erythroleukemia cells.

Journal: Oncogene 20030109

Title: Induction of apoptosis by combined treatment with differentiation-inducing agents and interferon-alpha in human lung cancer cells.

Journal: Anticancer research 20030101

Title: [Effects of HMBA on the expression of cell-cycle-associated genes in human hepatocarcinoma SMMC-7721 cells].

Journal: Shi yan sheng wu xue bao 20020901

Title: Targeted removal of PML-RARalpha protein is required prior to inhibition of histone deacetylase for overcoming all-trans retinoic acid differentiation resistance in acute promyelocytic leukemia.

Journal: Blood 20020801

Title: Structure, expression, and functional characterization of the mouse CLP-1 gene.

Journal: Gene 20020612

Title: Specific PAF antagonist WEB-2086 induces terminal differentiation of murine and human leukemia cells.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20020501

Title: [Effect of hexamethylene bisacetamine on proliferation and apoptosis of human leukemia cells in vitro and relevant mechanisms].

Journal: Zhonghua yi xue za zhi 20020425

Title: Membrane phospholipid reorganization differentially regulates metallothionein and heme oxygenase by heme-hemopexin.

Journal: DNA and cell biology 20020401

Title: A Myb dependent pathway maintains Friend murine erythroleukemia cells in an immature and proliferating state.

Journal: Oncogene 20020314

Title: Surface antigens of human embryonic stem cells: changes upon differentiation in culture.

Journal: Journal of anatomy 20020301

Title: [Effects of hexamethylene bisacetamide on related genes expression of apoptosis and cell proliferating in human mucoepidermoid carcinoma cell line MEC-1].

Journal: Zhonghua kou qiang yi xue za zhi = Zhonghua kouqiang yixue zazhi = Chinese journal of stomatology 20020301

Title: New designed HMBA agents as inducers of erythroleukemia cell differentiation.

Journal: Chinese medical sciences journal = Chung-kuo i hsueh k'o hsueh tsa chih 20020301

Title: [Differentiation of human hepatocarcinoma SMMC-7721 cells induced by HMBA].

Journal: Shi yan sheng wu xue bao 20011201

Title: [Regulation of Chinese medicine bailong and hexamethylene bisacetamide on cyclin dependent kinase inhibitor P16 genes in human cancer cell].

Journal: Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20011001

Title: Hexamethylene bisacetamide protects peritoneal mesothelial cells from glucose.

Journal: Kidney international 20010901

Title: Calretinin and calretinin-22k increase resistance toward sodium butyrate-induced differentiation in CaCo-2 colon adenocarcinoma cells.

Journal: Experimental cell research 20010801

Title: Establishment of a consistent L929 bioassay system for TNF-alpha quantitation to evaluate the effect of lipopolysaccharide, phytomitogens and cytodifferentiation agents on cytotoxicity of TNF-alpha secreted by adherent human mononuclear cells.

Journal: Mediators of inflammation 20010801

Title: Induction of telomerase activity during development of human mast cells from peripheral blood CD34+ cells: comparisons with tumor mast-cell lines.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20010601

Title: Expression of microtubule-associated protein 2 in benign and malignant melanocytes: implications for differentiation and progression of cutaneous melanoma.

Journal: The American journal of pathology 20010601

Title: Structural characterization of erythroid and megakaryocytic differentiation in Friend erythroleukemia cells.

Journal: Experimental hematology 20010501

Title: [Regulative effects of bailong and Hexamethylene bisacetamide on growth and phenotype of human gastric cancer cells in cell cycle].

Journal: Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20010501

Title: Regulation of tyrosinase-related protein-2 (TYRP2) in human melanocytes: relationship to growth and morphology.

Journal: Pigment cell research 20010401

Title: [Study on common character of regulative molecular mechanism of Chinese drug bailong and hexamethylen bisacetamide in human cancer cell cycle and their oncogene and tumor suppressor gene expression].

Journal: Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20010401

Title: Growth inhibition and differentiation of C6 glioma cells on treatment with hmba.

Journal: Cell biology international 20010101

Title: A novel system to identify Myb target promoters in friend murine erythroleukemia cells.

Journal: Blood cells, molecules & diseases 20010101

Title: Induction of apoptosis in U937 human leukemia cells by suberoylanilide hydroxamic acid (SAHA) proceeds through pathways that are regulated by Bcl-2/Bcl-XL, c-Jun, and p21CIP1, but independent of p53.

Journal: Oncogene 19991125

Title: Effects of oxygen radical scavengers on connexins 32 and 26 expression in primary cultures of adult rat hepatocytes.

Journal: Carcinogenesis 19960301

Title: All-trans retinoic acid induces monocyte growth factor receptor (c-fms) gene expression in HL-60 leukemia cells.

Journal: Leukemia 19930301

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Tags:3073-59-4 Molecular Formula|3073-59-4 MDL|3073-59-4 SMILES|3073-59-4 N,N'-(Hexane-1,6-diyl)diacetamide