DHA
General
Type : Natural, Fatty acid
Chemical_Nomenclature : (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Canonical SMILES : CC\/C=CC\/C=CC\/C=CC\/C=CC\/C=CC\/C=CCCC(=O)O
InChI : InChI=1S\/C22H32O2\/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24\/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)\/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChIKey : MBMBGCFOFBJSGT-KUBAVDMBSA-N
Other name(s) : Docosahexaenoic acid || Doconexent || Doconexento || Doconexentum || Doxonexent || AquaGrow Advantage || Martek DHA HM || Ropufa 60 || CHEBI:36005 || CHEMBL367149 || DB03756 || docosahexaenoic acid(DHA) || SCHEMBL18274991
MW : 328.5
Formula : C22H32O2
CAS_number : 6217-54-5
PubChem : 445580
UniChem : MBMBGCFOFBJSGT-KUBAVDMBSA-N
Target
Structures : No structure
Families : No family
References (39)
| Title : Novel lipase-catalyzed synthesis of structured lipids from DHA-enriched glycerides and capric acid - Cho_2025_Food.Sci.Biotechnol_34_3077 |
| Author(s) : Cho Y , Lee C , Lee J , Kim HW , Kim IH |
| Ref : Food Sci Biotechnol , 34 :3077 , 2025 |
| Abstract : |
| PubMedSearch : Cho_2025_Food.Sci.Biotechnol_34_3077 |
| PubMedID: 40894969 |
| Title : Novel lipase-catalyzed synthesis of structured lipids from DHA-enriched glycerides and capric acid - Cho_2025_Food.Sci.Biotechnol_34_3077 |
| Author(s) : Cho Y , Lee C , Lee J , Kim HW , Kim IH |
| Ref : Food Sci Biotechnol , 34 :3077 , 2025 |
| Abstract : |
| PubMedSearch : Cho_2025_Food.Sci.Biotechnol_34_3077 |
| PubMedID: 40894969 |
| Title : Novel lipase-catalyzed synthesis of structured lipids from DHA-enriched glycerides and capric acid - Cho_2025_Food.Sci.Biotechnol_34_3077 |
| Author(s) : Cho Y , Lee C , Lee J , Kim HW , Kim IH |
| Ref : Food Sci Biotechnol , 34 :3077 , 2025 |
| Abstract : |
| PubMedSearch : Cho_2025_Food.Sci.Biotechnol_34_3077 |
| PubMedID: 40894969 |
| Title : Utilization of Fusarium Solani lipase for enrichment of polyunsaturated Omega-3 fatty acids - de Carvalho Silva_2024_Braz.J.Microbiol__ |
| Author(s) : de Carvalho Silva AK , Lima FJL , Borges KRA , Wolff LAS , de Andrade MS , Alves RNS , Cordeiro CB , Da Silva M , Nascimento M , da Silva Esposito T , de Barros Bezerra GF |
| Ref : Braz J Microbiol , : , 2024 |
| Abstract : |
| PubMedSearch : de Carvalho Silva_2024_Braz.J.Microbiol__ |
| PubMedID: 38874742 |
| Title : Utilization of Fusarium Solani lipase for enrichment of polyunsaturated Omega-3 fatty acids - de Carvalho Silva_2024_Braz.J.Microbiol__ |
| Author(s) : de Carvalho Silva AK , Lima FJL , Borges KRA , Wolff LAS , de Andrade MS , Alves RNS , Cordeiro CB , Da Silva M , Nascimento M , da Silva Esposito T , de Barros Bezerra GF |
| Ref : Braz J Microbiol , : , 2024 |
| Abstract : |
| PubMedSearch : de Carvalho Silva_2024_Braz.J.Microbiol__ |
| PubMedID: 38874742 |
| Title : Utilization of Fusarium Solani lipase for enrichment of polyunsaturated Omega-3 fatty acids - de Carvalho Silva_2024_Braz.J.Microbiol__ |
| Author(s) : de Carvalho Silva AK , Lima FJL , Borges KRA , Wolff LAS , de Andrade MS , Alves RNS , Cordeiro CB , Da Silva M , Nascimento M , da Silva Esposito T , de Barros Bezerra GF |
| Ref : Braz J Microbiol , : , 2024 |
| Abstract : |
| PubMedSearch : de Carvalho Silva_2024_Braz.J.Microbiol__ |
| PubMedID: 38874742 |
| Title : Bioimprinted lipase-catalyzed synthesis of medium- and long-chain structured lipids rich in docosahexaenoic acid for infant formula - Zou_2023_Food.Chem_424_136450 |
| Author(s) : Zou X , Su H , Zhang F , Zhang H , Yeerbolati Y , Xu X , Chao Z , Zheng L , Jiang B |
| Ref : Food Chem , 424 :136450 , 2023 |
| Abstract : |
| PubMedSearch : Zou_2023_Food.Chem_424_136450 |
| PubMedID: 37247604 |
| Title : Green biosynthesis of rare DHA-phospholipids by lipase-catalyzed transesterification with edible algal oil in solvent-free system and catalytic mechanism study - Zhang_2023_Front.Bioeng.Biotechnol_11_1158348 |
| Author(s) : Zhang T , Li B , Wang Z , Hu D , Zhang X , Zhao B , Wang J |
| Ref : Front Bioeng Biotechnol , 11 :1158348 , 2023 |
| Abstract : |
| PubMedSearch : Zhang_2023_Front.Bioeng.Biotechnol_11_1158348 |
| PubMedID: 37064237 |
| Title : Green biosynthesis of DHA-phospholipids in tailor-made supersaturated DHA aqueous solution and catalytic mechanism study - Zhang_2023_Food.Chem_431_137164 |
| Author(s) : Zhang T , Wang J , Zhao Y , Wang Z , Hu D , Liu Y , Zhang X , Li H , Zhao B , Li B |
| Ref : Food Chem , 431 :137164 , 2023 |
| Abstract : |
| PubMedSearch : Zhang_2023_Food.Chem_431_137164 |
| PubMedID: 37607420 |
| Title : Bioimprinted lipase-catalyzed synthesis of medium- and long-chain structured lipids rich in docosahexaenoic acid for infant formula - Zou_2023_Food.Chem_424_136450 |
| Author(s) : Zou X , Su H , Zhang F , Zhang H , Yeerbolati Y , Xu X , Chao Z , Zheng L , Jiang B |
| Ref : Food Chem , 424 :136450 , 2023 |
| Abstract : |
| PubMedSearch : Zou_2023_Food.Chem_424_136450 |
| PubMedID: 37247604 |
| Title : Green biosynthesis of rare DHA-phospholipids by lipase-catalyzed transesterification with edible algal oil in solvent-free system and catalytic mechanism study - Zhang_2023_Front.Bioeng.Biotechnol_11_1158348 |
| Author(s) : Zhang T , Li B , Wang Z , Hu D , Zhang X , Zhao B , Wang J |
| Ref : Front Bioeng Biotechnol , 11 :1158348 , 2023 |
| Abstract : |
| PubMedSearch : Zhang_2023_Front.Bioeng.Biotechnol_11_1158348 |
| PubMedID: 37064237 |
| Title : Green biosynthesis of DHA-phospholipids in tailor-made supersaturated DHA aqueous solution and catalytic mechanism study - Zhang_2023_Food.Chem_431_137164 |
| Author(s) : Zhang T , Wang J , Zhao Y , Wang Z , Hu D , Liu Y , Zhang X , Li H , Zhao B , Li B |
| Ref : Food Chem , 431 :137164 , 2023 |
| Abstract : |
| PubMedSearch : Zhang_2023_Food.Chem_431_137164 |
| PubMedID: 37607420 |
| Title : Bioimprinted lipase-catalyzed synthesis of medium- and long-chain structured lipids rich in docosahexaenoic acid for infant formula - Zou_2023_Food.Chem_424_136450 |
| Author(s) : Zou X , Su H , Zhang F , Zhang H , Yeerbolati Y , Xu X , Chao Z , Zheng L , Jiang B |
| Ref : Food Chem , 424 :136450 , 2023 |
| Abstract : |
| PubMedSearch : Zou_2023_Food.Chem_424_136450 |
| PubMedID: 37247604 |
| Title : Green biosynthesis of rare DHA-phospholipids by lipase-catalyzed transesterification with edible algal oil in solvent-free system and catalytic mechanism study - Zhang_2023_Front.Bioeng.Biotechnol_11_1158348 |
| Author(s) : Zhang T , Li B , Wang Z , Hu D , Zhang X , Zhao B , Wang J |
| Ref : Front Bioeng Biotechnol , 11 :1158348 , 2023 |
| Abstract : |
| PubMedSearch : Zhang_2023_Front.Bioeng.Biotechnol_11_1158348 |
| PubMedID: 37064237 |
| Title : Green biosynthesis of DHA-phospholipids in tailor-made supersaturated DHA aqueous solution and catalytic mechanism study - Zhang_2023_Food.Chem_431_137164 |
| Author(s) : Zhang T , Wang J , Zhao Y , Wang Z , Hu D , Liu Y , Zhang X , Li H , Zhao B , Li B |
| Ref : Food Chem , 431 :137164 , 2023 |
| Abstract : |
| PubMedSearch : Zhang_2023_Food.Chem_431_137164 |
| PubMedID: 37607420 |
| Title : Chain-locked precursor ion scanning based HPLC-MS\/MS for in-depth molecular analysis of lipase-catalyzed transesterification of structured phospholipids containing w-3 fatty acyl chains - Zhang_2022_Food.Chem_399_133982 |
| Author(s) : Zhang M , Wang P , Jin D , Jian S , Wu J , Huang M , Xie H , Zhao Q , Yang H , Luo P , Yuan H , Xue J , Shen Q |
| Ref : Food Chem , 399 :133982 , 2022 |
| Abstract : |
| PubMedSearch : Zhang_2022_Food.Chem_399_133982 |
| PubMedID: 36027811 |
| Title : Chain-locked precursor ion scanning based HPLC-MS\/MS for in-depth molecular analysis of lipase-catalyzed transesterification of structured phospholipids containing w-3 fatty acyl chains - Zhang_2022_Food.Chem_399_133982 |
| Author(s) : Zhang M , Wang P , Jin D , Jian S , Wu J , Huang M , Xie H , Zhao Q , Yang H , Luo P , Yuan H , Xue J , Shen Q |
| Ref : Food Chem , 399 :133982 , 2022 |
| Abstract : |
| PubMedSearch : Zhang_2022_Food.Chem_399_133982 |
| PubMedID: 36027811 |
| Title : Chain-locked precursor ion scanning based HPLC-MS\/MS for in-depth molecular analysis of lipase-catalyzed transesterification of structured phospholipids containing w-3 fatty acyl chains - Zhang_2022_Food.Chem_399_133982 |
| Author(s) : Zhang M , Wang P , Jin D , Jian S , Wu J , Huang M , Xie H , Zhao Q , Yang H , Luo P , Yuan H , Xue J , Shen Q |
| Ref : Food Chem , 399 :133982 , 2022 |
| Abstract : |
| PubMedSearch : Zhang_2022_Food.Chem_399_133982 |
| PubMedID: 36027811 |
| Title : Ethyl esters production catalyzed by immobilized lipases is influenced by n-hexane and ter-amyl alcohol as organic solvents - Borges_2020_Bioprocess.Biosyst.Eng_43_2107 |
| Author(s) : Borges JP , Quilles Junior JC , Moreno-Perez S , Fernandez-Lorente G , Boscolo M , Gomes E , da Silva R , Bocchini DA , Guisan JM |
| Ref : Bioprocess Biosyst Eng , 43 :2107 , 2020 |
| Abstract : |
| PubMedSearch : Borges_2020_Bioprocess.Biosyst.Eng_43_2107 |
| PubMedID: 32594315 |
| Title : Ethyl esters production catalyzed by immobilized lipases is influenced by n-hexane and ter-amyl alcohol as organic solvents - Borges_2020_Bioprocess.Biosyst.Eng_43_2107 |
| Author(s) : Borges JP , Quilles Junior JC , Moreno-Perez S , Fernandez-Lorente G , Boscolo M , Gomes E , da Silva R , Bocchini DA , Guisan JM |
| Ref : Bioprocess Biosyst Eng , 43 :2107 , 2020 |
| Abstract : |
| PubMedSearch : Borges_2020_Bioprocess.Biosyst.Eng_43_2107 |
| PubMedID: 32594315 |
| Title : Ethyl esters production catalyzed by immobilized lipases is influenced by n-hexane and ter-amyl alcohol as organic solvents - Borges_2020_Bioprocess.Biosyst.Eng_43_2107 |
| Author(s) : Borges JP , Quilles Junior JC , Moreno-Perez S , Fernandez-Lorente G , Boscolo M , Gomes E , da Silva R , Bocchini DA , Guisan JM |
| Ref : Bioprocess Biosyst Eng , 43 :2107 , 2020 |
| Abstract : |
| PubMedSearch : Borges_2020_Bioprocess.Biosyst.Eng_43_2107 |
| PubMedID: 32594315 |
| Title : Yarrowia lipolytica lipase Lip2: an efficient enzyme for the production of concentrates of docosahexaenoic acid ethyl ester - Casas-Godoy_2014_J.Biotechnol_180_30 |
| Author(s) : Casas-Godoy L , Meunchan M , Cot M , Duquesne S , Bordes F , Marty A |
| Ref : J Biotechnol , 180 :30 , 2014 |
| Abstract : |
| PubMedSearch : Casas-Godoy_2014_J.Biotechnol_180_30 |
| PubMedID: 24657346 |
| Gene_locus related to this paper: yarli-lip2 |
| Title : Yarrowia lipolytica lipase Lip2: an efficient enzyme for the production of concentrates of docosahexaenoic acid ethyl ester - Casas-Godoy_2014_J.Biotechnol_180_30 |
| Author(s) : Casas-Godoy L , Meunchan M , Cot M , Duquesne S , Bordes F , Marty A |
| Ref : J Biotechnol , 180 :30 , 2014 |
| Abstract : |
| PubMedSearch : Casas-Godoy_2014_J.Biotechnol_180_30 |
| PubMedID: 24657346 |
| Gene_locus related to this paper: yarli-lip2 |
| Title : Yarrowia lipolytica lipase Lip2: an efficient enzyme for the production of concentrates of docosahexaenoic acid ethyl ester - Casas-Godoy_2014_J.Biotechnol_180_30 |
| Author(s) : Casas-Godoy L , Meunchan M , Cot M , Duquesne S , Bordes F , Marty A |
| Ref : J Biotechnol , 180 :30 , 2014 |
| Abstract : |
| PubMedSearch : Casas-Godoy_2014_J.Biotechnol_180_30 |
| PubMedID: 24657346 |
| Gene_locus related to this paper: yarli-lip2 |
| Title : Efficient display of active Geotrichum sp. lipase on Pichia pastoris cell wall and its application as a whole-cell biocatalyst to enrich EPA and DHA in fish oil - Pan_2012_J.Agric.Food.Chem_60_9673 |
| Author(s) : Pan XX , Xu L , Zhang Y , Xiao X , Wang XF , Liu Y , Zhang HJ , Yan YJ |
| Ref : Journal of Agricultural and Food Chemistry , 60 :9673 , 2012 |
| Abstract : |
| PubMedSearch : Pan_2012_J.Agric.Food.Chem_60_9673 |
| PubMedID: 22934819 |
| Title : Efficient display of active Geotrichum sp. lipase on Pichia pastoris cell wall and its application as a whole-cell biocatalyst to enrich EPA and DHA in fish oil - Pan_2012_J.Agric.Food.Chem_60_9673 |
| Author(s) : Pan XX , Xu L , Zhang Y , Xiao X , Wang XF , Liu Y , Zhang HJ , Yan YJ |
| Ref : Journal of Agricultural and Food Chemistry , 60 :9673 , 2012 |
| Abstract : |
| PubMedSearch : Pan_2012_J.Agric.Food.Chem_60_9673 |
| PubMedID: 22934819 |
| Title : Efficient display of active Geotrichum sp. lipase on Pichia pastoris cell wall and its application as a whole-cell biocatalyst to enrich EPA and DHA in fish oil - Pan_2012_J.Agric.Food.Chem_60_9673 |
| Author(s) : Pan XX , Xu L , Zhang Y , Xiao X , Wang XF , Liu Y , Zhang HJ , Yan YJ |
| Ref : Journal of Agricultural and Food Chemistry , 60 :9673 , 2012 |
| Abstract : |
| PubMedSearch : Pan_2012_J.Agric.Food.Chem_60_9673 |
| PubMedID: 22934819 |
| Title : Preparation of a crosslinked bioimprinted lipase for enrichment of polyunsaturated fatty acids from fish processing waste - Yan_2010_Appl.Biochem.Biotechnol_162_757 |
| Author(s) : Yan J , Li L , Tang Q , Jiang M , Jiang S |
| Ref : Appl Biochem Biotechnol , 162 :757 , 2010 |
| Abstract : |
| PubMedSearch : Yan_2010_Appl.Biochem.Biotechnol_162_757 |
| PubMedID: 20101527 |
| Title : Retailoring docosahexaenoic acid-containing phospholipid species during impaired neurogenesis following omega-3 alpha-linolenic acid deprivation - Brand_2010_J.Neurochem_114_1393 |
| Author(s) : Brand A , Crawford MA , Yavin E |
| Ref : Journal of Neurochemistry , 114 :1393 , 2010 |
| Abstract : |
| PubMedSearch : Brand_2010_J.Neurochem_114_1393 |
| PubMedID: 20557429 |
| Title : Retailoring docosahexaenoic acid-containing phospholipid species during impaired neurogenesis following omega-3 alpha-linolenic acid deprivation - Brand_2010_J.Neurochem_114_1393 |
| Author(s) : Brand A , Crawford MA , Yavin E |
| Ref : Journal of Neurochemistry , 114 :1393 , 2010 |
| Abstract : |
| PubMedSearch : Brand_2010_J.Neurochem_114_1393 |
| PubMedID: 20557429 |
| Title : Preparation of a crosslinked bioimprinted lipase for enrichment of polyunsaturated fatty acids from fish processing waste - Yan_2010_Appl.Biochem.Biotechnol_162_757 |
| Author(s) : Yan J , Li L , Tang Q , Jiang M , Jiang S |
| Ref : Appl Biochem Biotechnol , 162 :757 , 2010 |
| Abstract : |
| PubMedSearch : Yan_2010_Appl.Biochem.Biotechnol_162_757 |
| PubMedID: 20101527 |
| Title : Preparation of a crosslinked bioimprinted lipase for enrichment of polyunsaturated fatty acids from fish processing waste - Yan_2010_Appl.Biochem.Biotechnol_162_757 |
| Author(s) : Yan J , Li L , Tang Q , Jiang M , Jiang S |
| Ref : Appl Biochem Biotechnol , 162 :757 , 2010 |
| Abstract : |
| PubMedSearch : Yan_2010_Appl.Biochem.Biotechnol_162_757 |
| PubMedID: 20101527 |
| Title : Retailoring docosahexaenoic acid-containing phospholipid species during impaired neurogenesis following omega-3 alpha-linolenic acid deprivation - Brand_2010_J.Neurochem_114_1393 |
| Author(s) : Brand A , Crawford MA , Yavin E |
| Ref : Journal of Neurochemistry , 114 :1393 , 2010 |
| Abstract : |
| PubMedSearch : Brand_2010_J.Neurochem_114_1393 |
| PubMedID: 20557429 |
| Title : Lipase specificity towards eicosapentaenoic acid and docosahexaenoic acid depends on substrate structure - Lyberg_2008_Biochim.Biophys.Acta_1784_343 |
| Author(s) : Lyberg AM , Adlercreutz P |
| Ref : Biochimica & Biophysica Acta , 1784 :343 , 2008 |
| Abstract : |
| PubMedSearch : Lyberg_2008_Biochim.Biophys.Acta_1784_343 |
| PubMedID: 18067872 |
| Title : Lipase specificity towards eicosapentaenoic acid and docosahexaenoic acid depends on substrate structure - Lyberg_2008_Biochim.Biophys.Acta_1784_343 |
| Author(s) : Lyberg AM , Adlercreutz P |
| Ref : Biochimica & Biophysica Acta , 1784 :343 , 2008 |
| Abstract : |
| PubMedSearch : Lyberg_2008_Biochim.Biophys.Acta_1784_343 |
| PubMedID: 18067872 |
| Title : Lipase specificity towards eicosapentaenoic acid and docosahexaenoic acid depends on substrate structure - Lyberg_2008_Biochim.Biophys.Acta_1784_343 |
| Author(s) : Lyberg AM , Adlercreutz P |
| Ref : Biochimica & Biophysica Acta , 1784 :343 , 2008 |
| Abstract : |
| PubMedSearch : Lyberg_2008_Biochim.Biophys.Acta_1784_343 |
| PubMedID: 18067872 |
| Title : Ethyl esterification of docosahexaenoic acid in an organic solvent-free system with immobilized Candida antarctica lipase - Shimada_2001_J.Biosci.Bioeng_92_19 |
| Author(s) : Shimada Y , Watanabe Y , Sugihara A , Baba T , Ooguri T , Moriyama S , Terai T , Tominaga Y |
| Ref : J Biosci Bioeng , 92 :19 , 2001 |
| Abstract : |
| PubMedSearch : Shimada_2001_J.Biosci.Bioeng_92_19 |
| PubMedID: 16233051 |
| Gene_locus related to this paper: canar-LipB |
| Title : Ethyl esterification of docosahexaenoic acid in an organic solvent-free system with immobilized Candida antarctica lipase - Shimada_2001_J.Biosci.Bioeng_92_19 |
| Author(s) : Shimada Y , Watanabe Y , Sugihara A , Baba T , Ooguri T , Moriyama S , Terai T , Tominaga Y |
| Ref : J Biosci Bioeng , 92 :19 , 2001 |
| Abstract : |
| PubMedSearch : Shimada_2001_J.Biosci.Bioeng_92_19 |
| PubMedID: 16233051 |
| Gene_locus related to this paper: canar-LipB |
| Title : Ethyl esterification of docosahexaenoic acid in an organic solvent-free system with immobilized Candida antarctica lipase - Shimada_2001_J.Biosci.Bioeng_92_19 |
| Author(s) : Shimada Y , Watanabe Y , Sugihara A , Baba T , Ooguri T , Moriyama S , Terai T , Tominaga Y |
| Ref : J Biosci Bioeng , 92 :19 , 2001 |
| Abstract : |
| PubMedSearch : Shimada_2001_J.Biosci.Bioeng_92_19 |
| PubMedID: 16233051 |
| Gene_locus related to this paper: canar-LipB |