JP6558925B2 - ケトオクタデカジエン酸の製造方法 - Google Patents
ケトオクタデカジエン酸の製造方法 Download PDFInfo
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- JP6558925B2 JP6558925B2 JP2015062418A JP2015062418A JP6558925B2 JP 6558925 B2 JP6558925 B2 JP 6558925B2 JP 2015062418 A JP2015062418 A JP 2015062418A JP 2015062418 A JP2015062418 A JP 2015062418A JP 6558925 B2 JP6558925 B2 JP 6558925B2
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- acid
- ketooctadecadienoic
- oil
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- manganese
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Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
ケトオクタデカジエン酸のLC−MS/MS分析は、以下の条件で行った。
LC条件:
移動相A;水(0.1%ギ酸を含む)
移動相B;アセトニトリル(0.1%ギ酸を含む)
グラジエント条件;移動相A50%(0分)−80%(14分)−99%(17〜18分)−50%(19分)
カラム温度;50℃
カラム;YMC−Triart C18(100×2.0mm、1.9m)
流速;0.3mL/分
インジェクション量;5μL
分析時間;38分
Scans in Period;1069
Relative Start Time;1100.00msec
Scan Type;MRM
Polarity;Negative
・13−oxo−ODA
Q1mass;293.30
Q3mass;113.00
Dwell(msec);500.00
・9−oxo−ODA
Q1mass;293.10
Q3mass;185.20
Dwell(msec);500.00
製造した反応液について、熟練したパネル5名による香りの官能評価を実施した。官能評価の基準を以下に示す。官能評価がA又はBであれば、酸化劣化臭が少なく、副生成物が抑制されていると評価することができる。
(油の酸化劣化臭)
A:油の酸化劣化臭がわずかであるか、ほとんど感じられない。
B:油の酸化劣化臭が弱い。
C:油の酸化劣化臭がやや強い。
D:油の酸化劣化臭が強い。
0.2M炭酸ナトリウム溶液及び0.2M炭酸水素ナトリウム溶液を7:3(v:v)となるように混合し、pHが10.2の緩衝液(炭酸ナトリウム/炭酸水素ナトリウム緩衝液)を調製した。大豆粉末として生大豆(国産、フクユタカ)をミキサーで破砕し粉末化したものを用いた。破砕の際は、熱の発生を抑制するため、温度上昇に注意しながら間欠的に破砕した。緩衝液1L、大豆粉末20g、及びリノール酸(和光純薬社製、特級試薬)28gを、2.5Lミニジャーファーメンターに仕込み、5℃の温度条件で3時間通気攪拌を行った。その後、実施例1〜3及び比較例1〜2では、マンガン含有酵母を10g(1%w/v;セティ社販売品、マンガン5%含有)添加し、下記表1に示した温度及び反応時間にて通気攪拌を行った。比較例3ではマンガン含有酵母を添加せずに、下記表1に示した温度及び反応時間にて通気攪拌を行った。反応液中に生成した13−oxo−ODAの含有量及び官能評価の結果を表1に示す。
0.2M炭酸ナトリウム溶液及び0.2M炭酸水素ナトリウム溶液を7:3(v:v)となるように混合し、pHが10.2の緩衝液(炭酸ナトリウム/炭酸水素ナトリウム緩衝液)を調製した。大豆粉末として生大豆(国産、フクユタカ)をミキサーで破砕し粉末化したものを用いた。破砕の際は、熱の発生を抑制するため、温度上昇に注意しながら間欠的に破砕した。緩衝液1L、大豆粉末20g、及びリノール酸(和光純薬社製、特級試薬)28gを、2.5Lミニジャーファーメンターに仕込み、5℃の温度条件で、実施例4及び5については3時間通気攪拌を行い、実施例6については4時間通気攪拌を行った。その後、実施例4ではマンガン含有酵母を10g(1%w/v)添加し、実施例5では亜鉛含有酵母10g(1%w/v;メディエンス社販売品、亜鉛10%含有)を添加し、実施例6では鉄含有酵母10g(1%w/v;セティ社販売品、鉄5%含有)を添加し、下記表2に示した温度及び反応時間にて通気攪拌を行った。反応液中に生成した13−oxo−ODA及び9−oxo−ODAの含有量及び官能評価の結果を表2に示す。
0.2M炭酸ナトリウム溶液及び0.2M炭酸水素ナトリウム溶液を7:3(v:v)となるように混合し、pHが10.2の緩衝液(炭酸ナトリウム/炭酸水素ナトリウム緩衝液)を調製した。大豆粉末として生大豆(国産、フクユタカ)をミキサーで破砕し粉末化したものを用いた。破砕の際は、熱の発生を抑制するため、温度上昇に注意しながら間欠的に破砕した。水0.5L、リパーゼ(リパーゼOF、名糖産業社製)0.15g、及び大豆油(大豆白絞油、昭和産業社製)を、2.5Lミニジャーファーメンターに仕込み、43〜48℃の温度条件で攪拌しながら24時間リパーゼ反応を行った。その後、5℃まで冷却し、実施例7及び8では大豆粉末添加後、3時間の反応を行った。リパーゼ反応後のpHはそれぞれ、pH7.5、pH7.6であった。実施例9〜12では大豆粉末添加後、1VVM(volume per volume per minute:1分間に供給する培地1L当たりの通気量)にて6時間の反応を行った。下記表3に示す金属又は金属酵母を添加し、表3に示した温度及び反応時間にて通気攪拌を行った。反応液中に生成した13−oxo−ODA及び9−oxo−ODAの含有量及び官能評価の結果を表3に示す。なお、硫酸マンガン一水和物は、和光純薬社製のものを用いた。硫酸鉄は、関東化学社製の食品添加物を用いた。
Claims (9)
- マンガンの存在下、且つ20℃未満の温度で、リノール酸を含む原料にリポキシゲナーゼを含む酵素材料を作用させる工程を備える、ケトオクタデカジエン酸の製造方法であって、
前記酵素材料が、大豆、トウモロコシ、エンドウ、オオムギ、コムギ、ピーナッツ、ジャガイモ及びトマトからなる群より選ばれる少なくとも1種の材料を含むか、又はこれらの材料から精製されたリポキシゲナーゼを含む、製造方法。 - 前記マンガンが、マンガン含有酵母により供給される、請求項1に記載の製造方法。
- 前記ケトオクタデカジエン酸が、13−オキソ−9,11−オクタデカジエン酸である、請求項1又は2に記載の製造方法。
- 前記温度が、0℃以上15℃以下である、請求項1〜3のいずれか一項に記載の製造方法。
- 前記酵素材料が、大豆粉末である、請求項1〜4のいずれか一項に記載の製造方法。
- 前記原料が、食用油又はその加工物である、請求項1〜5のいずれか一項に記載の製造方法。
- 前記食用油が、大豆油である、請求項6に記載の製造方法。
- 前記工程の前に、前記原料にエステラーゼを作用させる工程をさらに備える、請求項6又は7に記載の製造方法。
- 前記エステラーゼが、リパーゼである、請求項8に記載の製造方法。
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