JPS6114160B2 - - Google Patents

Info

Publication number: JPS6114160B2
Authority: JP; Japan
Prior art keywords: glucose; glucopyranosyl; methanol; glycoside; compound
Prior art date: 1976-09-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP51108499A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5334966A (en

Inventor

Tsunematsu Takemoto

Tadashi Nakajima

Shigenobu Arihara

Megumi Okudaira

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nippon Shoji Co Ltd

Original Assignee

Nippon Shoji Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-09-09

Filing date

1976-09-09

Publication date

1986-04-17

1976-09-09 Application filed by Nippon Shoji Co Ltd filed Critical Nippon Shoji Co Ltd

1976-09-09 Priority to JP10849976A priority Critical patent/JPS5334966A/ja

1976-12-29 Priority to US05/755,425 priority patent/US4084010A/en

1978-03-31 Publication of JPS5334966A publication Critical patent/JPS5334966A/ja

1986-04-17 Publication of JPS6114160B2 publication Critical patent/JPS6114160B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 32
125000000188 beta-D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 16
150000002482 oligosaccharides Polymers 0.000 claims description 16
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 13
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000008103 glucose Substances 0.000 claims description 8
125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 7
235000003599 food sweetener Nutrition 0.000 claims description 3
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 3
239000003765 sweetening agent Substances 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
229930182470 glycoside Natural products 0.000 description 30
150000002338 glycosides Chemical class 0.000 description 28
239000000126 substance Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
238000004809 thin layer chromatography Methods 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
235000009508 confectionery Nutrition 0.000 description 9
239000000284 extract Substances 0.000 description 9
102000016679 alpha-Glucosidases Human genes 0.000 description 8
108010028144 alpha-Glucosidases Proteins 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
235000019605 sweet taste sensations Nutrition 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
235000013399 edible fruits Nutrition 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
108010059892 Cellulase Proteins 0.000 description 4
229930091371 Fructose Natural products 0.000 description 4
239000005715 Fructose Substances 0.000 description 4
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
229930006000 Sucrose Natural products 0.000 description 4
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
229940106157 cellulase Drugs 0.000 description 4
235000013305 food Nutrition 0.000 description 4
239000000499 gel Substances 0.000 description 4
241000411851 herbal medicine Species 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000002994 raw material Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
229960004793 sucrose Drugs 0.000 description 4
-1 β-D-glucopyranosyl Chemical group 0.000 description 4
241000219104 Cucurbitaceae Species 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
238000010828 elution Methods 0.000 description 3
239000012046 mixed solvent Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
238000011109 contamination Methods 0.000 description 2
229940124600 folk medicine Drugs 0.000 description 2
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000001397 quillaja saponaria molina bark Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229930182490 saponin Natural products 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000003648 triterpenes Chemical class 0.000 description 2
238000005406 washing Methods 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
241001409321 Siraitia grosvenorii Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000011171 Thladiantha grosvenorii Nutrition 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
238000010411 cooking Methods 0.000 description 1
238000003795 desorption Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
235000011194 food seasoning agent Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
229920001542 oligosaccharide Polymers 0.000 description 1
239000002245 particle Substances 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000014214 soft drink Nutrition 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
150000003445 sucroses Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000003523 triterpene group Chemical group 0.000 description 1
239000011345 viscous material Substances 0.000 description 1

Landscapes

Seasonings (AREA)
Saccharide Compounds (AREA)
Steroid Compounds (AREA)

JP10849976A 1976-01-01 1976-09-09 Novel glycoside with sweetening action and rerated substance Granted JPS5334966A (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
JP10849976A JPS5334966A (en)	1976-09-09	1976-09-09	Novel glycoside with sweetening action and rerated substance
US05/755,425 US4084010A (en)	1976-01-01	1976-12-29	Glycosides having sweetness

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP10849976A JPS5334966A (en)	1976-09-09	1976-09-09	Novel glycoside with sweetening action and rerated substance

Publications (2)

Publication Number	Publication Date
JPS5334966A JPS5334966A (en)	1978-03-31
JPS6114160B2 true JPS6114160B2 (2)	1986-04-17

Family

ID=14486316

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10849976A Granted JPS5334966A (en)	1976-01-01	1976-09-09	Novel glycoside with sweetening action and rerated substance

Country Status (1)

Country	Link
JP (1)	JPS5334966A (2)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3502587B2 (ja) *	2000-01-31	2004-03-02	サラヤ株式会社	高純度羅漢果配糖体を含有する甘味料組成物
EP2529633B1 (de) *	2011-06-01	2014-08-06	Symrise AG	Oral konsumierbare Zubereitungen umfassend bestimmte süß schmeckende Triterpene und Triterpenglycoside
KR20160093704A (ko) *	2013-12-05	2016-08-08	아날리티콘 디스커버리 게엠베하	감미료들 또는 감미료 증진제들로서 신규한 트리테르펜-글리코사이드

1976
- 1976-09-09 JP JP10849976A patent/JPS5334966A/ja active Granted

Also Published As

Publication number	Publication date
JPS5334966A (en)	1978-03-31

Publication	Publication Date	Title
US4084010A (en)	1978-04-11	Glycosides having sweetness
CN101970450B (zh)	2015-02-18	新蛇菊苷a衍生产物和制备方法
EP3766362B1 (en)	2022-12-28	Method of production of steviol glycoside sweeteners with improved flavor profiles
Abou-Arab et al.	2010	Physico-chemical assessment of natural sweeteners steviosides produced from Stevia rebaudiana Bertoni plant
DE60200749T2 (de)	2004-12-02	Süssungsmittel und Verfahren zu deren Herstellung
CN106061987B (zh)	2023-12-01	甜菊糖苷的分离、离析和表征方法
JP2898688B2 (ja)	1999-06-02	高甘味糖付加ステビア甘味料及びその製法
Kiribuchi et al.	1966	Separation of soybean sterols by florisil chromatography and characterization of acylated steryl glucoside
YOSHIKAWA et al.	1996	Bioactive saponins and glycosides. V. Acylated polyhydroxyolean-12-ene triterpene oligoglycosides, camelliasaponins A1, A2, B1, B2, C1, and C2, from the seeds of Camellia japonica L.: structures and inhibitory activity on alcohol absorption
Rout et al.	2006	The structure of a polysaccharide from Fraction-II of an edible mushroom, Pleurotus florida
CN110719738B (zh)	2023-06-09	组合物
CA1148936A (en)	1983-06-28	Triterpenic saponin having pharmacological potency
Friedman et al.	1993	Kinetics of acid-catalyzed hydrolysis of carbohydrate groups of potato glycoalkaloids. alpha.-chaconine and. alpha.-solanine
JP2001211854A (ja)	2001-08-07	高純度羅漢果配糖体を含有する甘味料組成物
JP2022525490A (ja)	2022-05-17	モグロシド化合物およびその使用
US5198427A (en)	1993-03-30	Natural intense sweeteners
CN104926907B (zh)	2017-01-04	天然甜味剂c-21甾体皂苷类化合物及其制备方法与应用
JPS6050798B2 (ja)	1985-11-11	甘味作用を有する新規な配糖体
US20220211088A1 (en)	2022-07-07	Scutellaria compositions and methods for taste modulation
JPS6040822B2 (ja)	1985-09-12	甘味物の製造方法
JPS5948059A (ja)	1984-03-19	変性ステビオシド
Zarrelli et al.	2014	History of gymnemic acid, a molecule that does not exist
JPS61265068A (ja)	1986-11-22	抗肥満食品
JPH0694473B2 (ja)	1994-11-24	β−グルコシルルブソサイド及その製造方法及これを利用した甘味料
Lyantagaye	2013	Two new pro-apoptotic glucopyranosides from Tulbaghia violacea