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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/08/11 23:07:03」(JST)

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Kojic acid is a chelation agent produced by several species of fungi, especially Aspergillus oryzae, which has the Japanese common name koji.^[2]^[3] Kojic acid is a by-product in the fermentation process of malting rice, for use in the manufacturing of sake, the Japanese rice wine.^[2] It is a mild inhibitor of the formation of pigment in plant and animal tissues, and is used in food and cosmetics to preserve or change colors of substances.^[4] It forms a bright red complex with ferric ions.

Biosynthesis

¹³C-Labeling studies have revealed at least two pathways to kojic acid. In the usual route, dehydratase enzymes convert glucose to kojic acid. Pentoses are also viable precursors in which case dihydroxyacetone is invoked as an intermediate.^[2]

Applications

Kojic acid may be used on cut fruits to prevent oxidative browning, in seafood to preserve pink and red colors, and in cosmetics to lighten skin. As an example of the latter, it is used to treat skin diseases like melasma.^[5] Kojic acid also has antibacterial and antifungal properties.^{[citation needed]} The cocrystals of kojic acid with quercetin were found to have two times better cytotoxic activity to human cervical cancer cells (HeLa) and human colon cancer cells (Caco-2) in comparison with quercetin itself.^[6]

Protective effects from radiation-induced damage

Kojic acid appears to possess marked protective (radioresistance) effects from radiation-induced damage. It increased the 30-day survival rate of mice after exposed to a lethal dose of gamma radiation and had significant radioprotective effects on the hematopoietic system, the immune system and DNA of mice exposed to a 4 Gy sublethal dose of radiation. Pretreatment with Kojic acid has been shown to protect Chinese hamster ovary cells against ionizing radiation-induced damage. Dogs pretreated with kojic acid after whole-body exposure to a lethal dose of 3 Gy gamma radiation had a 51-day survival rate of 66.7% versus the dogs in the 3 Gy irradiation only group, which all died within 16 days of postirradiation.^[7]

References

^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
^ ^a ^b ^c Bentley, R. (2006). "From miso, sake and shoyu to cosmetics: a century of science for kojic acid". Nat. Prod. Rep. 23: 1046–1062. doi:10.1039/b603758p.
^ Yabuta T (1924). "The constitution of kojic acid, a gamma-pyrone derivative formed by Aspergillus oryzae from carbohydrates". Journal of the Chemical Society. 125: 575–587. doi:10.1039/ct9242500575.
^ Kojic acid and enzymatic browning
^ Melasma, American Academy of Dermatology
^ Veverka, M., Dubaj, T., Gallovič, J., Jorík, V., Veverková, E., Danihelová, M., & Šimon, P. (2015). Cocrystals of quercetin: synthesis, characterization, and screening of biological activity. Monatshefte für Chemie-Chemical Monthly,146(1), 99-109 doi:10.1007/s00706-014-1314-6
^ Wang, Kai; Li, Peng-Fei; Han, Chun-Guang; Du, Li; Liu, Chao; Hu, Ming; Lian, Shi-Jie; Liu, Yong-Xue (2014). "Protective Effects of Kojic Acid on the Periphery Blood and Survival of Beagle Dogs after Exposure to a Lethal Dose of Gamma Radiation". Radiation Research. 182 (6): 666–673. doi:10.1667/RR13823.1.

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UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 肝斑 melasma
2. 炎症後色素沈着過剰症 postinflammatory hyperpigmentation
3. Acquired hyperpigmentation disorders
4. 偽髭毛嚢炎 pseudofolliculitis barbae
5. ケロイドおよび肥厚性瘢痕 keloids and hypertrophic scars

English Journal

Novel hydroxypyridinone derivatives containing an oxime ether moiety: Synthesis, inhibition on mushroom tyrosinase and application in anti-browning of fresh-cut apples.

Shao LL1, Wang XL2, Chen K1, Dong XW3, Kong LM1, Zhao DY1, Hider RC4, Zhou T5.
Food chemistry.Food Chem.2018 Mar 1;242:174-181. doi: 10.1016/j.foodchem.2017.09.054. Epub 2017 Sep 12.
PMID 29037675

Design, synthesis, kinetic mechanism and molecular docking studies of novel 1-pentanoyl-3-arylthioureas as inhibitors of mushroom tyrosinase and free radical scavengers.

Larik FA1, Saeed A2, Channar PA1, Muqadar U1, Abbas Q3, Hassan M3, Seo SY3, Bolte M4.
European journal of medicinal chemistry.Eur J Med Chem.2017 Dec 1;141:273-281. doi: 10.1016/j.ejmech.2017.09.059. Epub 2017 Sep 29.
PMID 29040952

Intra-species Volatile Interactions Affects Growth Rates and Exometabolomes in Aspergillus oryzae KCCM 60345.

Singh D1, Lee CH1.
Journal of microbiology and biotechnology.J Microbiol Biotechnol.2017 Nov 15. doi: 10.4014/jmb.1711.11005. [Epub ahead of print]
PMID 29141132

Japanese Journal

1P-013 麹菌おけるコウジ酸生産量の相違の解析(遺伝子工学,一般講演)

日本生物工学会大会講演要旨集 67, 92, 2015-09-25
NAID 110010008793

Effect of kojic acid-grafted-chitosan oligosaccharides as a novel antibacterial agent on cell membrane of gram-positive and gram-negative bacteria(BIOCHEMICAL ENGINEERING)

Journal of bioscience and bioengineering 120(3), 335-339, 2015-09
NAID 110009987523

コウジ酸の顔面黄ぐすみに対する改善効果

西日本皮膚科 77(3), 244-249, 2015
NAID 130005101064

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★リンクテーブル★

リンク元	「麹酸」「コウジ酸」

「麹酸」

Kojic acid
Names
	IUPAC name 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
	Other names Kojic acid, 5-Hydroxy-2-(hydroxymethyl)-4-pyrone, 2-Hydroxymethyl-5-hydroxy-γ-pyrone
Identifiers
CAS Number	501-30-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:43572 ;
ChemSpider	3708 ;
DrugBank	DB01759 ;
ECHA InfoCard	100.007.203
EC Number	207-922-4
KEGG	C14516 ;
PubChem CID	3840;
RTECS number	UQ0875000
UNII	6K23F1TT52 ;
	InChI InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2 Key: BEJNERDRQOWKJM-UHFFFAOYSA-N ; InChI=1/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2 ;
	SMILES O=C1/C=C(\O/C=C1/O)CO ;
Properties
Chemical formula	C6H6O4
Molar mass	142.11 g/mol
Appearance	white
Melting point	152 to 155 °C (306 to 311 °F; 425 to 428 K)
Solubility in water	Slight
Acidity (pKa)	9.40
Hazards
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S22, S24/25
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

　　[★]

英: kojic acid
関: コウジ酸

「コウジ酸」

　　[★]

英: kojic acid
関: 麹酸

[1] Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.

[Bentley-2] Bentley, R. (2006). "From miso, sake and shoyu to cosmetics: a century of science for kojic acid". Nat. Prod. Rep. 23: 1046–1062. doi:10.1039/b603758p.

[3] Yabuta T (1924). "The constitution of kojic acid, a gamma-pyrone derivative formed by Aspergillus oryzae from carbohydrates". Journal of the Chemical Society. 125: 575–587. doi:10.1039/ct9242500575.

[4] Kojic acid and enzymatic browning

[5] Melasma, American Academy of Dermatology

[6] Veverka, M., Dubaj, T., Gallovič, J., Jorík, V., Veverková, E., Danihelová, M., & Šimon, P. (2015). Cocrystals of quercetin: synthesis, characterization, and screening of biological activity. Monatshefte für Chemie-Chemical Monthly,146(1), 99-109 doi:10.1007/s00706-014-1314-6

[7] Wang, Kai; Li, Peng-Fei; Han, Chun-Guang; Du, Li; Liu, Chao; Hu, Ming; Lian, Shi-Jie; Liu, Yong-Xue (2014). "Protective Effects of Kojic Acid on the Periphery Blood and Survival of Beagle Dogs after Exposure to a Lethal Dose of Gamma Radiation". Radiation Research. 182 (6): 666–673. doi:10.1667/RR13823.1.

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kojic acid