GB947643A - Substituted chroman compounds - Google Patents

Substituted chroman compounds

Info

Publication number
GB947643A
GB947643A GB1789360A GB1789360A GB947643A GB 947643 A GB947643 A GB 947643A GB 1789360 A GB1789360 A GB 1789360A GB 1789360 A GB1789360 A GB 1789360A GB 947643 A GB947643 A GB 947643A
Authority
GB
United Kingdom
Prior art keywords
compound
acid
compounds
coenzyme
iii
Prior art date
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
GB1789360A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB947643A publication Critical patent/GB947643A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids

Abstract

The invention comprises chroman compounds of formula: <FORM:0947643/C2/1> wherein R is a hydrogen atom or an acyl radical. The compounds are prepared from Coenzyme Q by reactions which are shown in the following scheme: <FORM:0947643/C2/2> <FORM:0947643/C2/3> <FORM:0947643/C2/4> <FORM:0947643/C2/5> Compound II (Coenzyme Q) may be heated under reduced pressure to form compound I directly without intermediate formation of compound III. Alternatively compound II is reduced to the corresponding hydroquinone III which is heated in the presence of an acid catalyst to produce compound I. Specified reducing agents are sodium borohydride, metal acid mixtures and sodium hydrosulphite. Specified acid catalysts are p-toluene sulphonic acid, sulphuric acid, ferric acid, zinc chloride and stannous chloride. In a preferred process compound II is refluxed in glacial acetic acid to which stannous chloride is added to effect both the reduction and cyclisation steps and yield compound I. Compound I may be catalytically hydrogenated to give compound IV. Compounds I and IV may be acylated using carboxylic acids having up to 9 carbon atoms e.g. acetic and p-nitrobenzoic. The compounds show anti-oxidant activity in fats and oils. The preparation of the compounds is described in examples.
GB1789360A 1959-05-25 1960-05-20 Substituted chroman compounds Expired GB947643A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81530759A 1959-05-25 1959-05-25
US1958160A 1960-04-14 1960-04-14

Publications (1)

Publication Number Publication Date
GB947643A true GB947643A (en) 1964-01-22

Family

ID=26692363

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1789360A Expired GB947643A (en) 1959-05-25 1960-05-20 Substituted chroman compounds

Country Status (2)

Country Link
BE (1) BE591122A (en)
GB (1) GB947643A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003006409A1 (en) * 2001-07-13 2003-01-23 Kaneka Corporation Method of producing reduced coenzyme q10 crystals with excellent handling properties
WO2003006411A1 (en) 2001-07-13 2003-01-23 Kaneka Corporation Method of crystallizing reduced coenzyme q10 from aqueous solution
WO2003006408A1 (en) 2001-07-13 2003-01-23 Kaneka Corporation Method of producing reduced coenzyme q10 using solvent with high oxidation-protective effect
WO2003006410A1 (en) * 2001-07-13 2003-01-23 Kaneka Corporation Method of producing reduced coenzyme q10 as oily product
WO2004063131A1 (en) * 2003-01-10 2004-07-29 Kaneka Corporation Method of purifying reduced coenzyme q
FR2893026A1 (en) * 2005-11-08 2007-05-11 Polaris Soc Par Actions Simpli New fat-soluble esters of cathechin, useful as antioxidants in foods, pharmaceuticals and cosmetics, particularly in fish oils, prepared using long-chain aliphatic carboxylic acids
CN100503543C (en) * 2001-07-13 2009-06-24 钟渊化学工业株式会社 Method of producing reduced coenzyme q10 as oily product
EP2380568A1 (en) * 2001-10-10 2011-10-26 Kaneka Corporation Method of producing and crystallizing reduced coenzyme Q10
WO2022229214A1 (en) * 2021-04-28 2022-11-03 Dsm Ip Assets B.V. Ring closure of benzoquinones containing an unsaturated side chain using a base in two-phase system
WO2022229215A1 (en) * 2021-04-28 2022-11-03 Dsm Ip Assets B.V. Ring closure of benzoquinones containing an unsaturated side chain using a basic catalyst

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7524993B2 (en) 2001-07-13 2009-04-28 Kaneka Corporation Method of producing reduced coenzyme Q10 as oily product
EP1415969A1 (en) * 2001-07-13 2004-05-06 Kaneka Corporation Method of producing reduced coenzyme q10 using solvent with high oxidation-protective effect
WO2003006409A1 (en) * 2001-07-13 2003-01-23 Kaneka Corporation Method of producing reduced coenzyme q10 crystals with excellent handling properties
WO2003006410A1 (en) * 2001-07-13 2003-01-23 Kaneka Corporation Method of producing reduced coenzyme q10 as oily product
CN100503543C (en) * 2001-07-13 2009-06-24 钟渊化学工业株式会社 Method of producing reduced coenzyme q10 as oily product
EP3321248A3 (en) * 2001-07-13 2018-06-06 Kaneka Corporation Method of producing reduced coenzyme q10 using solvent with high oxidation-protective effect
EP1415969A4 (en) * 2001-07-13 2005-04-27 Kaneka Corp Method of producing reduced coenzyme q10 using solvent with high oxidation-protective effect
US7145044B2 (en) 2001-07-13 2006-12-05 Kaneka Corporation Method of producing reduced coenzyme Q10 using solvent with high oxidation-protective effect
US7208639B2 (en) 2001-07-13 2007-04-24 Kaneka Corporation Method of producing reduced coenzyme Q10 as oily product
CN101774996B (en) * 2001-07-13 2015-02-11 钟渊化学工业株式会社 Method of producing reduced coenzyme Q10 using solvent with high oxidation-protective effect
US8853464B2 (en) 2001-07-13 2014-10-07 Kaneka Corporation Method of producing reduced coenzyme Q10 crystals with excellent handling properties
EP2228360A1 (en) * 2001-07-13 2010-09-15 Kaneka Corporation Method of producing reduced coenzyme Q10 using solvent with high oxidation-protective effect
AU2002318845B2 (en) * 2001-07-13 2008-09-11 Kaneka Corporation Method of producing reduced coenzyme Q10 as oily product
AU2002318843B2 (en) * 2001-07-13 2008-10-30 Kaneka Corporation Method of producing reduced coenzyme Q10 using solvent with high oxidation-protective effect
WO2003006408A1 (en) 2001-07-13 2003-01-23 Kaneka Corporation Method of producing reduced coenzyme q10 using solvent with high oxidation-protective effect
WO2003006411A1 (en) 2001-07-13 2003-01-23 Kaneka Corporation Method of crystallizing reduced coenzyme q10 from aqueous solution
AU2002318844B2 (en) * 2001-07-13 2008-06-05 Kaneka Corporation Method of producing reduced coenzyme Q10 crystals with excellent handling properties
US8003828B2 (en) 2001-07-13 2011-08-23 Kaneka Corporation Method of producing reduced coenzyme Q10 crystals with excellent handling properties
EP2402303A3 (en) * 2001-07-13 2012-04-25 Kaneka Corporation A reduced coenzyme Q10 crystal
CN102381948A (en) * 2001-10-10 2012-03-21 株式会社钟化 Method of stabilizing reduced coenzyme Q10
EP2380568A1 (en) * 2001-10-10 2011-10-26 Kaneka Corporation Method of producing and crystallizing reduced coenzyme Q10
US8703155B2 (en) 2001-10-10 2014-04-22 Kaneka Corporation Method of stabilizing reduced coenzyme q10
CN102381948B (en) * 2001-10-10 2014-10-01 株式会社钟化 Method of stabilizing reduced coenzyme Q10
US9532957B2 (en) 2001-10-10 2017-01-03 Kaneka Corporation Method of stabilizing reduced coenzyme Q10
CN100344595C (en) * 2003-01-10 2007-10-24 株式会社钟化 Method of purifying reduced coenzyme Q
WO2004063131A1 (en) * 2003-01-10 2004-07-29 Kaneka Corporation Method of purifying reduced coenzyme q
FR2893026A1 (en) * 2005-11-08 2007-05-11 Polaris Soc Par Actions Simpli New fat-soluble esters of cathechin, useful as antioxidants in foods, pharmaceuticals and cosmetics, particularly in fish oils, prepared using long-chain aliphatic carboxylic acids
WO2022229214A1 (en) * 2021-04-28 2022-11-03 Dsm Ip Assets B.V. Ring closure of benzoquinones containing an unsaturated side chain using a base in two-phase system
WO2022229215A1 (en) * 2021-04-28 2022-11-03 Dsm Ip Assets B.V. Ring closure of benzoquinones containing an unsaturated side chain using a basic catalyst

Also Published As

Publication number Publication date
BE591122A (en) 1960-11-23

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