Kojic Acid
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| Category | Antibiotics |
| Catalog number | BBF-01896 |
| CAS | 501-30-4 |
| Molecular Weight | 142.11 |
| Molecular Formula | C6H6O4 |
| Purity | ≥99% |
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Description
It is produced from the Aspergillus parasiticus. Kojic Acid has anti-leptospira effect with MIC of 1-10 μg/mL. It is also a tyrosinase inhibitor, which acts as a chelating agent that inhibits the production of melanin and should help chloasma in vitro.
Specification
| Synonyms | 5-Hydroxy-2-(hydroxymethyl)-4-pyrone; 4H-PYRAN-4-ONE, 5-HYDROXY-2-(HYDROXYMETHYL)-; 2-Hydroxymethyl-5-hydroxy-gamma-pyrone; NSC 1942 |
| Storage | RT. |
| IUPAC Name | 5-hydroxy-2-(hydroxymethyl)pyran-4-one |
| Canonical SMILES | C1=C(OC=C(C1=O)O)CO |
| InChI | InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2 |
| InChI Key | BEJNERDRQOWKJM-UHFFFAOYSA-N |
| Source | Kojic acid is a chelation agent and mycotoxin produced by several species of Aspergillus, Acetobacter, and Penicillium fungi, especially Aspergillus oryzae, which has the Japanese common name koji. |
Properties
| Appearance | Colorless Acicular Crystalline |
| Boiling Point | 401.67°C at 760 mmHg |
| Melting Point | 152-155°C (lit.) |
| Flash Point | 179.9ºC |
| Density | 1.54 g/cm3 |
| Solubility | Soluble in water, acetone (freely soluble), ethanol (freely soluble), methanol, DMSO, ethyl acetate (slightly soluble), chloroform (slightly soluble), pydidine (slightly soluble), and ether (slightly soluble). Insoluble in benzene. |
| LogP | -0.64 |
Toxicity
| Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
| Mechanism Of Toxicity | Kojic acid acts as a competitive and reversible inhibitor of animal and plant polyphenol oxidases (tyrosinases), xanthine oxidase, and D- and some L-amino acid oxidases. Inhibition of tyrosinases prevents melanosis, while inhibition of the oxidases prevents metabolism of certain amino acids. Kojic acid also reversibly affects thyroid function by inhibiting iodine uptake, leading to decreases in thyroid hormones T3 and T4 and increases in thyroid-stimulating hormone (TSH). Increased TSH from pituitary gland in turn stimulates thyroid hyperplasia. |
Reference Reading
1.Periorbital Hyperpigmentation: A Comprehensive Review.
Sarkar R1, Ranjan R1, Garg S1, Garg VK1, Sonthalia S1, Bansal S1. J Clin Aesthet Dermatol. 2016 Jan;9(1):49-55.
Periorbital hyperpigmentation is a commonly encountered condition. There is very little scientific data available on the clinical profile and pathogenesis of periorbital hyperpigmentation. Periorbital hyperpigmentation is caused by various exogenous and endogenous factors. The causative factors include genetic or heredity, excessive pigmentation, postinflammatory hyperpigmentation secondary to atopic and allergic contact dermatitis, periorbital edema, excessive vascularity, shadowing due to skin laxity and tear trough associated with aging. There are a number of treatment options available for periorbital hyperpigmentation. Among the available alternatives to treat dark circles are topical depigmenting agents, such as hydroquinone, kojic acid, azelaic acid, and topical retinoic acid, and physical therapies, such as chemical peels, surgical corrections, and laser therapy, most of which are tried scientifically for melasma, another common condition of hyperpigmentation that occurs on the face.
2.In vitro and in silico studies of the inhibitory effects of some novel kojic acid derivatives on tyrosinase enzyme.
Asadzadeh A1, Sirous H2, Pourfarzam M2, Yaghmaei P1, Afshin F3. Iran J Basic Med Sci. 2016 Feb;19(2):132-44.
OBJECTIVES: Tyrosinase is a key enzyme in pigment synthesis. Overproduction of melanin in parts of the skin results in hyperpigmentation diseases. This enzyme is also responsible for the enzymatic browning in fruits and vegetables. Thus, its inhibitors are of great importance in the medical, cosmetic and agricultural fields.
3.Physiological Activities of Thiacremonone Produced in High Temperature and High Pressure Treated Garlic.
Woo KS1, Hwang IG2, Kim HY1, Lee SH3, Jeong HS3. Prev Nutr Food Sci. 2016 Mar;21(1):68-72. doi: 10.3746/pnf.2016.21.1.68. Epub 2016 Mar 31.
To examine the possibility of using thiacremonone isolated from high-temperature-high-pressure treated garlic, this study investigated the physiological activities properties. The IC50 values of hydroxyl, superoxide, hydrogen peroxide, and nitric oxide radical scavenging activities of thiacremonone were 92.50, 65.05, 12.60, and 81.53 μg/mL, respectively. On the other hand, the activities of vitamin C were 104.93, 99.43, 42.42, and 122.64 μg/mL, and the activities of butylated hydroxyanisole were 37.22, 68.45, 22.47, and 40.54 μg/mL, respectively. The IC50 value of ACE inhibition activities of thiacremonone and captoprill were 0.265 and 0.036 μg/mL, respectively. The IC50 value of xanthine oxidase inhibition activities of thiacremonone and allopurinol were 39.430 and 9.346 μg/mL, respectively. The IC50 value of tyrosinase inhibition activities of thiacremonone and kojic acid were 101.931 and 65.648 μg/mL, respectively.
4.Conformers of Kojic Acid and their Near-IR-Induced Conversions: Long-Range Intramolecular Vibrational Energy Transfer.
Halasa A, Reva I, Lapinski L, Rostkowska H, Fausto R, Nowak MJ. J Phys Chem A. 2016 Apr 12. [Epub ahead of print]
Conformational transformations were investigated for molecules of kojic acid trapped in low temperature argon and nitrogen matrixes. Two conformers, differing from each other by 120° rotation of the hydroxymethyl (-CH2OH) moiety, were found to be populated in freshly deposited matrixes, prior to any irradiation. Matrixes containing isolated monomers of kojic acid were irradiated with narrowband, tunable near-infrared (near-IR) laser light. Excitations at wavenumbers corresponding to the overtone of the stretching vibration of the OH bond of the hydroxymethyl group led to conversion of one of the observed conformers into another. The direction of this conformational transformation depended on the wavenumber (within the 7126-7115 cm-1 range) used for irradiation. The same conformational photoconversion was also observed to occur upon narrowband irradiation at much lower wavenumbers (from the 6468-6447 cm-1 range). Near-IR light from this range selectively excites overtone vibrations of the OH group directly attached to the heterocyclic ring.
Spectrum
GC-MS Spectrum - GC-MS (2 TMS)
Experimental Conditions
Instrument Type: GC-MS
Chromatography Type: GC
Retention Index Type: based on 9 n-alkanes (C10-C36)
Retention Index: 1684.55
Column Type: 5%-phenyl-95%-dimethylpolysiloxane capillary column
Derivative Type: 2 TMS
Derivative Formula: C12H22O4Si2
Derivative Molecular Weight: 286.472
Chromatography Type: GC
Retention Index Type: based on 9 n-alkanes (C10-C36)
Retention Index: 1684.55
Column Type: 5%-phenyl-95%-dimethylpolysiloxane capillary column
Derivative Type: 2 TMS
Derivative Formula: C12H22O4Si2
Derivative Molecular Weight: 286.472
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C6H6O4
Molecular Weight (Monoisotopic Mass): 142.0266 Da
Molecular Weight (Avergae Mass): 142.1094 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C6H6O4
Molecular Weight (Monoisotopic Mass): 142.0266 Da
Molecular Weight (Avergae Mass): 142.1094 Da
LC-MS/MS Spectrum - LC-ESI-QTOF , negative
Experimental Conditions
Instrument Type: LC-ESI-QTOF
Ionization Mode: negative
Ionization Mode: negative
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C6H6O4
Molecular Weight (Monoisotopic Mass): 142.0266 Da
Molecular Weight (Avergae Mass): 142.1094 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C6H6O4
Molecular Weight (Monoisotopic Mass): 142.0266 Da
Molecular Weight (Avergae Mass): 142.1094 Da
Mass Spectrum (Electron Ionization)
1H NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 1H
Frequency: 100
Nucleus: 1H
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
