CN112899315B - 一种稳定同位素标记的3-氯-1,2-丙二醇脂肪酸二酯的合成方法 - Google Patents
一种稳定同位素标记的3-氯-1,2-丙二醇脂肪酸二酯的合成方法 Download PDFInfo
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- CN112899315B CN112899315B CN201911274045.7A CN201911274045A CN112899315B CN 112899315 B CN112899315 B CN 112899315B CN 201911274045 A CN201911274045 A CN 201911274045A CN 112899315 B CN112899315 B CN 112899315B
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- stable isotope
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- propanediol
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 39
- 239000000194 fatty acid Substances 0.000 title claims abstract description 39
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 39
- -1 3-chloro-1, 2-propylene glycol fatty acid diester Chemical class 0.000 title claims abstract description 26
- 238000001308 synthesis method Methods 0.000 title claims abstract description 9
- 108090001060 Lipase Proteins 0.000 claims abstract description 20
- 239000004367 Lipase Substances 0.000 claims abstract description 20
- 102000004882 Lipase Human genes 0.000 claims abstract description 20
- 235000019421 lipase Nutrition 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 15
- 229960004063 propylene glycol Drugs 0.000 claims abstract description 13
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 8
- 108010048733 Lipozyme Proteins 0.000 claims description 6
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical group CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 claims description 6
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 108010084311 Novozyme 435 Proteins 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- BRLQWZUYTZBJKN-UXXIZXEISA-N 2-[chloro(dideuterio)methyl]-2,3,3-trideuteriooxirane Chemical compound [2H]C([2H])(Cl)C1([2H])OC1([2H])[2H] BRLQWZUYTZBJKN-UXXIZXEISA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000001948 isotopic labelling Methods 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 4
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 229940040461 lipase Drugs 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 2
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical class CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 description 2
- SGNZYJXNUURYCH-UHFFFAOYSA-N 5,6-dihydroxyindole Chemical compound C1=C(O)C(O)=CC2=C1NC=C2 SGNZYJXNUURYCH-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004750 isotope dilution mass spectroscopy Methods 0.000 description 2
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 2
- SSZWWUDQMAHNAQ-UXXIZXEISA-N 3-chloro-1,1,2,3,3-pentadeuteriopropane-1,2-diol Chemical compound [2H]C([2H])(O)C([2H])(O)C([2H])([2H])Cl SSZWWUDQMAHNAQ-UXXIZXEISA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 206010074268 Reproductive toxicity Diseases 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000007696 reproductive toxicity Effects 0.000 description 1
- 231100000372 reproductive toxicity Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/58—Esters of straight chain acids with eighteen carbon atoms in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
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CN201911274045.7A CN112899315B (zh) | 2019-12-12 | 2019-12-12 | 一种稳定同位素标记的3-氯-1,2-丙二醇脂肪酸二酯的合成方法 |
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CN201911274045.7A CN112899315B (zh) | 2019-12-12 | 2019-12-12 | 一种稳定同位素标记的3-氯-1,2-丙二醇脂肪酸二酯的合成方法 |
Publications (2)
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CN112899315A CN112899315A (zh) | 2021-06-04 |
CN112899315B true CN112899315B (zh) | 2022-11-18 |
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CN201911274045.7A Active CN112899315B (zh) | 2019-12-12 | 2019-12-12 | 一种稳定同位素标记的3-氯-1,2-丙二醇脂肪酸二酯的合成方法 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102093215A (zh) * | 2010-12-14 | 2011-06-15 | 王力清 | 一种制备高纯度3-氯-1,2-丙二醇脂肪酸酯的方法 |
CN102492741A (zh) * | 2011-12-22 | 2012-06-13 | 江南大学 | 一种氯丙醇酯的合成方法 |
CN105237338A (zh) * | 2015-08-31 | 2016-01-13 | 泰山医学院 | 一种连续合成高纯度3-氯-1,2-丙二醇的系统及方法 |
CN109867587A (zh) * | 2017-12-01 | 2019-06-11 | 中国科学院大连化学物理研究所 | 一种3氯-1,2-丙二醇的制备方法 |
-
2019
- 2019-12-12 CN CN201911274045.7A patent/CN112899315B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102093215A (zh) * | 2010-12-14 | 2011-06-15 | 王力清 | 一种制备高纯度3-氯-1,2-丙二醇脂肪酸酯的方法 |
CN102492741A (zh) * | 2011-12-22 | 2012-06-13 | 江南大学 | 一种氯丙醇酯的合成方法 |
CN105237338A (zh) * | 2015-08-31 | 2016-01-13 | 泰山医学院 | 一种连续合成高纯度3-氯-1,2-丙二醇的系统及方法 |
CN109867587A (zh) * | 2017-12-01 | 2019-06-11 | 中国科学院大连化学物理研究所 | 一种3氯-1,2-丙二醇的制备方法 |
Non-Patent Citations (2)
Title |
---|
A Scalable and Efficient Synthesis of 3-Chloro-1,2-propanediol;Ligia S. da Silveira Pinto et al.;《Organic Preparations and Procedures International》;20160518;第48卷;第319-320页 * |
Hexadecanoic acid, 1,1"-[2-(chloromethyl-d2)-1,2-ethanediyl-1,1,2-d3]ester;STN;《STN》;20090916 * |
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Effective date of registration: 20230519 Address after: Room 648, 649, 650, 651, Building 1, No. 299 Zhongchen Road, Songjiang District, Shanghai, 201613 Patentee after: Shanghai Ampere Trish Standard Technical Service Co.,Ltd. Address before: No.6059, Yexie Road, Zhangjiang Town, Shanghai Patentee before: Shanghai Anpu Experimental Technology Co.,Ltd. |
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Denomination of invention: A synthesis method of stable isotope labeled 3-chloro-1,2-propanediol fatty acid diesters Granted publication date: 20221118 Pledgee: Shanghai Rural Commercial Bank Co.,Ltd. Songjiang sub branch Pledgor: Shanghai Ampere Trish Standard Technical Service Co.,Ltd. Registration number: Y2024310000167 |
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