Kojic+Acid

toc =**Kojic Acid **=
 * By: Joe **



=General Information:=


 * = Compound Name ||= Kojic Acid ||
 * = IUPAC Name ||= 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one ||
 * = Common Name/Other Names ||= Kojic acid, 5-Hydroxy-2-(hydroxymethyl)-4-pyrone, 2-Hydroxymethyl-5-hydroxy-γ-pyrone ||
 * = Molecular Formula ||= C6H6O4 ||
 * = Molar Mass ||= 142.11 g/mol ||
 * = Density ||= 1.542 g/cm3 ||
 * = Melting/Boiling Point ||= Melting: 152-155 °C Boiling: 401.7 °C at 760 mmHg ||
 * = <span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; margin: 0px; padding: 0px;">Appearance ||= <span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; margin: 0px; padding: 0px;">Tan (after exposed to oxygen) or White Powder (pure form) ||
 * = <span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; margin: 0px; padding: 0px;">Solubility ||= <span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; margin: 0px; padding: 0px;">Soluble ||

= Historical Background and Discovery: = <span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; line-height: 48px;">﻿ **<span style="font-family: 'Comic Sans MS',cursive; font-size: 150%;">Kojic acid was first isolated by Dr. K Saito from //Aspergillus oryzae//, a type of mushroom that was found growing on steamed rice. He extracted the compound from the finely powdered fungus with hot water, and then this was extracted with ether yielding a crude product, which was purified by recrystallization from hot water. At first they believed it was oxalic, succinie, citric, malic, tartaric or benzoic acid, but tests proved these all false. They also thought it to be carbonic acid because of its melting points and behavior with ferric chloride. It was difficult to obtain more of the compound in sufficient enough quantities for testing, which lead to Dr. K Saito to stop his study. T. Yabuta, another scientist became interested in the study of this compound and undertook the preparation of numerous derivatives. From this, and from structural analysis, he discovered established its structure and named it "Kojic acid", probably from the origin of the compound. //Aspergillus oryzae//'s common name is "Koji" and this compound exhibited many acidic qualities. A few years later, F. Traeta-Mosca, while investigating the fermentation of fructose and sucrose with A. glaucus, isolated a compound which he first thought was y-lactone of trihydroxy hexadiene acid. Eventually, he observed the formation of the same compound during the fermentation of glycerol by the same mold. The chemistry of this was further studied and the conclusion was, it was a hydroxymethyl hydroxy y-pyrone. A comparison of the chemical behavior of Yabuta's kojic and with Traeta's y-lactone of trihydroxy hexadiene acid appears to indicate that they are the same substances. **





= = = Where is it found? How is it obtained? =

<span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; line-height: 48px;">**Kojic acid is primarily found in the culture "Koji" which is the Japanese name for cultures or bacterias. The cultures are primarily found in mushrooms, mainly from the species** **<span style="font-family: 'Comic Sans MS',cursive; font-size: 140%;">//Aspergillus oryzae//, or "Kojic Mushrooms." ** <span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; line-height: 48px;"> **It is also a byproduct in the process of making sake (A Japanese Wine) also known as malt rice fermentation. It can be removed from the rice with hot water, extracted with ether which is then purified by recrystallization from hot water. For a company, they use a process called "Membrane-surface liquid culture" which is a process of adding glucose to increase production to over 50 times than that obtained from the culture in shake flasks. Glucose is used as an energy/food for the cultures to grow off of.**



= Uses and Importance: =


 * <span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; line-height: 29px;">Kojic Acid can be used in skin care and in food preservation mostly. It can be found in lotions, soaps, creams and serums. In these products, the dosage is usually small, with a maximum concentration of 1%, however it is more common to see 0.2% concentration, to reduce the chance of side effects while still giving you the same effect. The most common use for it in skin care is to help lighten up the pigmentation of your skin, and it can help with skin disease such as melasma (dark skin discoloration). It also helps skin stay taunt and strong, helps remove blemishes, fights acne and can remove freckles. It works similar to other skin care compounds,but is more natural and safe in comparison to ones such as hydroquinone. Kojic acid is important because it is a more natural substance (98% pure/natural) and seems to have less side effects as apposed to stronger synthetics. Only minor cases of skin allergies or irritation have occurred. In the food industry it is used as a natural food preservative, keeping fruits from browning and keeping seafood's color from fading. It is also added to Japanese cuisine for added beneficial properties such as keeping cells healthy, and keeping the food fresh. Being a generally new product, kojic acid related beauty products are not as popular but are starting to grow in popularity. **

= Reactions/Composition/Structural Details: = <span style="font-family: 'Comic Sans MS',cursive;">**<span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; line-height: 48px;">﻿Percent Composition(by percents): Carbon 50.71%, Hydrogen 4.26% and Oxygen 45.03% ** <span style="font-family: 'Comic Sans MS',cursive;">**<span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; line-height: 48px;">Percent Composition(by numbers): Carbon 6/16, Hydrogen 6/16 and Oxygen 4/16. ** <span style="font-family: 'Comic Sans MS',cursive;">**<span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; line-height: 48px;">Percent Composition (by mass): 72.066g/142.11g (Carbon), 6.0474g/142.11g (Hydrogen), 63.9976g/142.11g (Oxygen). **

<span style="font-family: 'Comic Sans MS',cursive;">**<span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; line-height: 48px;">Reactions: The hydrogens in Kojic Acid easily dissociate from the hydroxyl groups in water making it soluble and giving it the ability to raise the concentration of hydrogen ions in a solution. It generates heat energy in water and reacts readily with alkaline-basic-substances to form neutral solutions. During the skin whitening process, kojic acids inhibit the enzyme "Tyrosinase" which regulates the formation of melanin or pigments in the skin. It gives off an intense red coloration with ferric chloride. ** <span style="font-family: 'Comic Sans MS',cursive;">**<span style="font-family: 'Comic Sans MS',cursive; font-size: 20px; line-height: 48px;">Structural Arrangement: The structure of Kojic Acid contains a five-carbon hexagonal ring, that has an oxygen atom completing the ring. The carbon atom opposite the oxygen atom, and the carbon next to it bonds with a second and third oxygen. The sixth carbon branches off from the ring, and bonds with a forth oxygen. The bond types are covalent. The bonding is non-metallic. **

=** 3-D Structure **:=

<span style="font-family: 'Comic Sans MS',cursive; font-size: 150%;">For Mac users, please save this file and open it with Imol, link for Imol found below this.(http://www.pirx.com/iMol/index.shtml)

= References: = <span style="font-family: 'Arial Black',Gadget,sans-serif;">"Kojic Acid." AuRas Optimum Skincare for Natural Beauty. Web. 24 Oct. 2010. <http://www.aurasnaturebeauty.org/kojicacid.htm>. <span style="font-family: 'Arial Black',Gadget,sans-serif;">"What Is Kojic Acid?" WiseGEEK: Clear Answers for Common Questions. Web. 24 Oct. 2010. <http://www.wisegeek.com/contest/what-is-kojic-acid.htm>. <span style="font-family: 'Arial Black',Gadget,sans-serif;">"Kojic Acid." Wikipedia, the Free Encyclopedia. Web. 24 Oct. 2010. <http://en.wikipedia.org/wiki/Kojic_acid>. <span style="font-family: 'Arial Black',Gadget,sans-serif;">"Products." The Skin Shoppe. Web. 24 Oct. 2010. <http://theskinshoppe.net/products.html>. <span style="font-family: 'Arial Black',Gadget,sans-serif;">"It's Ladies Choice » Kojic Acid Soap Review." It's Ladies Choice. Web. 24 Oct. 2010. <http://itsladieschoice.com/2010/06/kojic-acid-soap-review/>. <span style="font-family: 'Arial Black',Gadget,sans-serif;">Uforiabeauty.com. Web. 24 Oct. 2010. <http://uforiabeauty.com/uforia-ingredients.html>. <span style="font-family: 'Arial Black',Gadget,sans-serif;">"Is Kojic Acid Safe For Your Skin? | Healthy Life Journal." Enjoy Healthy Living, Live a Healthy Life, Sustain Good Health. Web. 24 Oct. 2010. <http://healthylifejournal.org/products/is-kojic-acid-safe-for-your-skin/>. <span style="font-family: 'Arial Black',Gadget,sans-serif;">"Molecular Structure of Kojic Acid | EHow.com." EHow | How To Do Just About Everything! | How To Videos & Articles. Web. 24 Oct. 2010. <http://www.ehow.com/facts_5808863_molecular-structure-kojic-acid.html>. <span style="font-family: 'Arial Black',Gadget,sans-serif;">"The Chemical Properties Of Kojic Acid | LIVESTRONG.COM." LIVESTRONG.COM - Health, Fitness, Lifestyle | LIVESTRONG.COM. Web. 24 Oct. 2010. <http://www.livestrong.com/article/123348-chemical-properties-kojic-acid/>. <span style="font-family: 'Arial Black',Gadget,sans-serif;"> "Kojic Acid - 501-30-4 - Catalog of Chemical Suppliers." ChemExper - Catalog of Chemicals Suppliers, Physical Characteristics and Search Engine. Web. 25 Oct. 2010. <http://www.chemexper.com/chemicals/supplier/cas/501-30-4.html>. <span style="font-family: 'Arial Black',Gadget,sans-serif;"> "IMol Home Page." Welcome to PIRX, Piotr Rotkiewicz's Website. Web. 25 Oct. 2010. <http://www.pirx.com/iMol/>. <span style="font-family: 'Arial Black',Gadget,sans-serif;"> "Kojic Acid." AuRas Optimum Skincare for Natural Beauty. Web. 26 Oct. 2010. <http://www.aurasnaturebeauty.org/kojicacid.htm>. <span style="font-family: 'Arial Black',Gadget,sans-serif;">"Kojic Acid - Works on Dark Spots and Pigmentated Skin." Facial Hyperpigmentation| Treatment for Pigmentation Problems. Web. 26 Oct. 2010. <http://www.hyperpigmentation-solutions.com/Kojic Acid.htm>. <span style="font-family: 'Arial Black',Gadget,sans-serif;"> Barham, H.N., and B.L. Smits. "Kojic Acid-A Review." Jstor: Trasactions of the Kansas Academy of Science 1903. Jstor. Web. 26 Oct. 2010. <http://www.jstor.org/pss/3625283>.

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