Kojic acid

Base Information

• Chemical Name: Kojic acid
• CAS No.: 501-30-4
• Deprecated CAS: 123712-78-7
• Molecular Formula: C6H6O4
• Molecular Weight: 142.111
• Hs Code.: 2941.90
• European Community (EC) Number: 207-922-4
• NSC Number: 1942
• UNII: 6K23F1TT52
• DSSTox Substance ID: DTXSID2040236
• Nikkaji Number: J1.564D
• Wikipedia: Kojic_acid
• Wikidata: Q416285
• RXCUI: 1426451
• Metabolomics Workbench ID: 45786
• ChEMBL ID: CHEMBL287556
• Mol file: 501-30-4.mol

Synonyms:5-((3-aminopropyl)phosphinooxy)-2-(hydroxymethyl)-4H-pyran-4-one;kojic acid;kojyl-APPA

Chemical Property of Kojic acid

Chemical Property:

• Appearance/Colour: Tan powder
• Melting Point: 152-155 °C
• Refractive Index: 1.4434 (estimate)
• Boiling Point: 401.7 °C at 760 mmHg
• PKA: 7.9(at 25℃)
• Flash Point: 179.9 °C
• PSA: 70.67000
• Density: 1.542 g/cm³
• LogP: -0.16230
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• Water Solubility.: SOLUBLE
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 142.02660867
• Heavy Atom Count: 10
• Complexity: 214

Purity/Quality:

99% ^*data from raw suppliers

Kojic acid 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40-68
• Safety Statements: 22-24/25-36/37-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(OC=C(C1=O)O)CO
• Chemical Composition and Structure: Kojic acid (KA) is a natural metabolite produced by fungi. Chemically, it is identified as 5-hydroxymethyl-pyrone. Its structure includes a hydroxymethyl group attached to a pyrone ring.
• Sources: Kojic acid is commonly produced by various species of fungi such as Aspergillus, Acetobacter, and Penicillium. It is also formed during the fermentation of foods like soy sauce, miso, and sake.
• Uses: Kojic acid and its derivatives find applications in medicine, cosmetics, food, agriculture, and chemical industries. In medicine, they are utilized for their antimicrobial, antiviral, antitumor, antidiabetic, anti-inflammatory, and anticancer properties. In cosmetics, they act as skin-lightening agents and antioxidants. In agriculture, kojic acid serves as an anti-browning agent for agricultural products.
• History and Development: Kojic acid was first marketed in 1955 by Charles Pfizer and Company, USA. Since then, its production has increased due to its commercial value in various industries. However, its carcinogenic potential led to its classification as a Class 3 carcinogen by the World Health Organization.
• Production Methods: Kojic acid is industrially produced by Aspergillus species in aerobic fermentation. Various carbon sources such as glucose, sucrose, and ethanol are utilized for its production.

Technology Process of Kojic acid

There total 17 articles about Kojic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

5-acetoxy-2-acetoxymethyl-4H-pyran-4-one (26209-93-8) → 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7)

Guidance literature:

With sodium methylate; In methanol; for 1h;

DOI:10.1039/c9cc07405h

Reference yield: 78.0%

chlorokojic acid (7559-81-1,54839-86-0) + acetone (67-64-1) → allomaltol (644-46-2) + 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7) + iodokojic acid (16065-34-2) + iodoacetone (3019-04-3)

Guidance literature:

With sodium iodide; at 45 ℃; for 24h;

DOI:10.1007/s007060070106

Reference yield: 70.0%

5-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)-2-(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)-4H-pyran-4-one → 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7)

Guidance literature:

With silica gel; In methanol; at 60 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c8cc08841a

upstream raw materials:

D-xylose

mannitol

D-sorbitol

D-galactitol

Downstream raw materials:

6-amino-7-cyano-2-hydroxymethyl-1'-methyl-4,2'-dioxo-4,8,2',3'-tetrahydrospiro[pyrano[3,2-b]pyran-8,3'-indole]

1,6-dimethyl-3-benzyloxy-pyridin-4(1H)-one-2-carboxy-(N-2'-hydroxyethyl)-amide

1,6-dimethyl-3-benzyloxy-pyridin-4(1H)-one-2-carboxy-(N-3'-pyridyl)-amide

1,6-dimethyl-3-benzyloxy-pyridin-4(1H)-one-2-carboxy-(N-phenyl)-amide

Refernces

• 1、 Lassfolk, Robert,Suonpa?, Anu,Birikh, Klara,Leino, Reko. "Chemo-enzymatic three-step conversion of glucose to kojic acid". supporting information. p. 14737 - 14740. Retrieved 2019/12/23.
• 2、 Uher, Michal,Szymońska, Joanna,Korenova, Anna,Tomasik, Piotr. "Re-examination of nucleophilic substitution in chlorokojic acid". . p. 301 - 307. Retrieved 2007/10/03.