JP2011079772A5 - - Google Patents
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- Publication number
- JP2011079772A5 JP2011079772A5 JP2009233040A JP2009233040A JP2011079772A5 JP 2011079772 A5 JP2011079772 A5 JP 2011079772A5 JP 2009233040 A JP2009233040 A JP 2009233040A JP 2009233040 A JP2009233040 A JP 2009233040A JP 2011079772 A5 JP2011079772 A5 JP 2011079772A5
- Authority
- JP
- Japan
- Prior art keywords
- ascorbic acid
- group
- glyceryl
- group represented
- salt
- 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.)
- Granted
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 33
- 229960005070 ascorbic acid Drugs 0.000 claims description 30
- 239000011668 ascorbic acid Substances 0.000 claims description 29
- 235000010323 ascorbic acid Nutrition 0.000 claims description 28
- -1 acylated derivative of glyceryl ascorbic acid Chemical compound 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- KQWQJCDIYBPYNT-ACFLWUFDSA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-4-(2,3-dihydroxypropoxy)-3-hydroxy-2h-furan-5-one Chemical compound OCC(O)COC1=C(O)[C@@H]([C@@H](O)CO)OC1=O KQWQJCDIYBPYNT-ACFLWUFDSA-N 0.000 description 5
- 230000003020 moisturizing effect Effects 0.000 description 5
- 210000003491 skin Anatomy 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- LDOBJFWHJVGAJK-AVVPKOCDSA-N [(2S)-2-[(2R)-4-(2,3-dihydroxypropoxy)-3-hydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(OCC(O)CO)=C1O LDOBJFWHJVGAJK-AVVPKOCDSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- IQHNEQZYMGDQDV-ACFLWUFDSA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3-(2,3-dihydroxypropoxy)-4-hydroxy-2h-furan-5-one Chemical compound OCC(O)COC1=C(O)C(=O)O[C@@H]1[C@@H](O)CO IQHNEQZYMGDQDV-ACFLWUFDSA-N 0.000 description 1
- SQYJRUFNBSYSAI-AZUAARDMSA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3-hexadecoxy-4-hydroxy-2h-furan-5-one Chemical compound CCCCCCCCCCCCCCCCOC1=C(O)C(=O)O[C@@H]1[C@@H](O)CO SQYJRUFNBSYSAI-AZUAARDMSA-N 0.000 description 1
- TVPCUVQDVRZTAL-UHFFFAOYSA-N 2-ethylhexanoyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(=O)C(CC)CCCC TVPCUVQDVRZTAL-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 239000002211 L-ascorbic acid Substances 0.000 description 1
- ACFGRWJEQJVZTM-LEJBHHMKSA-L Magnesium L-ascorbic acid-2-phosphate Chemical compound [Mg+2].OC[C@H](O)[C@H]1OC(=O)C(OP([O-])([O-])=O)=C1O ACFGRWJEQJVZTM-LEJBHHMKSA-L 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 206010047623 Vitamin C deficiency Diseases 0.000 description 1
- DXOSPYFPFHOQQC-CUROVOOSSA-N [(2S)-2-[(2R)-4-(2,3-dihydroxypropoxy)-3-hydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] butanoate Chemical compound CCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(OCC(O)CO)=C1O DXOSPYFPFHOQQC-CUROVOOSSA-N 0.000 description 1
- RCYZQGSSVFALOR-WQKBPTQTSA-N [(2S)-2-[(2R)-4-(2,3-dihydroxypropoxy)-3-hydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] octanoate Chemical compound CCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(OCC(O)CO)=C1O RCYZQGSSVFALOR-WQKBPTQTSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001124 arachidoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QWZBEFCPZJWDKC-UHFFFAOYSA-N hexadecanoyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCC QWZBEFCPZJWDKC-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940074358 magnesium ascorbate Drugs 0.000 description 1
- AIOKQVJVNPDJKA-ZZMNMWMASA-L magnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2h-furan-3-olate Chemical compound [Mg+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] AIOKQVJVNPDJKA-ZZMNMWMASA-L 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008099 melanin synthesis Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000016 octadecenoyl group Chemical group O=C([*])C([H])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 208000010233 scurvy Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009233040A JP5572358B2 (ja) | 2009-10-07 | 2009-10-07 | グリセリルアスコルビン酸アシル化誘導体又はその塩、その製造方法、及び化粧料。 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009233040A JP5572358B2 (ja) | 2009-10-07 | 2009-10-07 | グリセリルアスコルビン酸アシル化誘導体又はその塩、その製造方法、及び化粧料。 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011079772A JP2011079772A (ja) | 2011-04-21 |
| JP2011079772A5 true JP2011079772A5 (https=) | 2013-01-31 |
| JP5572358B2 JP5572358B2 (ja) | 2014-08-13 |
Family
ID=44074221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009233040A Active JP5572358B2 (ja) | 2009-10-07 | 2009-10-07 | グリセリルアスコルビン酸アシル化誘導体又はその塩、その製造方法、及び化粧料。 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5572358B2 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105878050A (zh) * | 2014-12-05 | 2016-08-24 | 江南大学 | 一种美白牙膏 |
| JP6649866B2 (ja) * | 2016-10-28 | 2020-02-19 | 株式会社成和化成 | コラーゲン産生促進効果に優れる化粧料又は皮膚外用剤 |
| JP2023144523A (ja) * | 2022-03-28 | 2023-10-11 | ピアス株式会社 | アトピー性皮膚炎改善剤、インターロイキン産生抑制剤、及び、インターロイキン遺伝子発現の抑制剤 |
| CN120174032A (zh) * | 2025-03-10 | 2025-06-20 | 安徽天寅生物技术有限公司 | 一种vc衍生物抗坏血酸甘油酯的合成工艺 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6185308A (ja) * | 1984-10-01 | 1986-04-30 | Kanebo Ltd | 皮膚化粧料 |
| EP2189452B1 (en) * | 2007-08-22 | 2012-11-21 | Seiwa Kasei Company, Limited | Ascorbic acid derivatives and salts thereof, process for their production, and cosmetic preparations thereof |
-
2009
- 2009-10-07 JP JP2009233040A patent/JP5572358B2/ja active Active
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