142-47-2 Usage
Uses
Used in Food Industry:
L-(+)Sodium glutamate is used as a flavor enhancer for foods in a concentration of about 0.3%. It is mainly used in oriental cuisine to enhance and impart a meaty flavor. MSG is used in large quantities as a complex flavor enhancer for gravies, meats, poultry, sauces, and in other combinations.
Used in Cosmetics Industry:
As a salt of amino acid, MSG is also safe in practices of use and concentration in cosmetics, such as skin care products. It is an amino acid with skin-conditioning, odor-masking, and hair-conditioning action.
Used in Tobacco Industry:
MSG is also used to enhance the taste of tobacco.
Used in Medical Treatment:
L-(+)Sodium glutamate is used to treat hepatic coma.
History of Development:
The best known and most widely used flavor enhancer is monosodium glutamate (MSG). It was first isolated as glutamic acid in 1866 by a German chemist, Ritthausen. Later, another chemist converted the acid to a sodium salt, monosodium glutamate. In 1908, a Japanese chemist, Dr. Kikunae Ikeda, discovered the flavor-enhancing properties of MSG. After isolating MSG, Dr. Ikeda developed a process for extracting it from wheat flour and other flours, and commercial production of MSG began in 1909.
Production:
MSG is commonly produced using a fermentation process using glucose (often sugar molasses) as a starting substance. Once the glucose is converted to glutamic acid, the glutamic acid is filtered, dissolved, and converted to monosodium glutamate by neutralization with sodium hydroxide. The monosodium glutamate solution is decolorized, and then the MSG is crystallized, dried, sieved, packed, and shipped.
Chemical Properties:
Monosodium glutamate is practically odorless and may have either a slightly sweet or slightly salty taste. It occurs as white free-flowing crystals or a crystalline powder. The addition of monosodium glutamate to food enhances several specific flavor characteristics, such as impact, body of fullness, continuity, mouth fullness, mildness, and complexity.
References
[1] Tetsuya Kawakita, L-Monosodium Glutamate (MSG), Kirk-Othmer Encyclopedia of Chemical Technology, 2000
[2] Leslie T. Webster and Charles S. Davidson, The effect of sodium glutamate on hepatic coma, The Journal of Clinical Investigation, 1956, vol. 35, 191-199
[3] DV Belsito, Safety Assessment of α-Amino Acids as Used in Cosmetics
Preparation
Monosodium glutamate is commonly produced by a fermentation process using glucose (often sugar molasses) as a
starting substance. Once the glucose is converted to glutamic acid, it is filtered, dissolved and converted to monosodium glutamate
by neutralization with sodium hydroxide. The monosodium glutamate solution is decolorized and then crystallized, dried, sieved,
packed and shipped
Production Methods
Monosodium glutamate is the monosodium salt of the naturally
occurring L-form of glutamic acid. It is commonly manufactured by
fermentation of carbohydrate sources such as sugar beet molasses.
In general, sugar beet products are used in Europe and the USA.
M
452 Monosodium Glutamate Other carbohydrate sources such as sugar cane and tapioca are used
in Asia.
Air & Water Reactions
Water soluble.
Reactivity Profile
L-(+)Sodium glutamate is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Fire Hazard
Flash point data are not available for L-(+)Sodium glutamate, but L-(+)Sodium glutamate is probably combustible.
Pharmaceutical Applications
Monosodium glutamate is used in oral pharmaceutical formulations
as a buffer and a flavor enhancer. For example, it is used with
sugar to improve the palatability of bitter-tasting drugs and can
reduce the metallic taste of iron-containing liquids. It has also been
used in subcutaneous live vaccine injections such as measles,
mumps, rubella and varicella-zoster live vaccine (ProQuad).
However, the most widespread use of monosodium glutamate is
as a flavor enhancer in food products. Typically, 0.2–0.9% is used in
normally salted foods, although products such as soy protein can
contain 10–30%. The use of monosodium glutamate in food
products has been controversial owing to the apparently high
number of adverse reactions attributed to the substance, which gives
rise to the so-called ‘Chinese Restaurant Syndrome’.The current consensus is that there is no clinically compelling
evidence to suggest that monosodium glutamate may be harmful at
the current levels used in foods.
Biochem/physiol Actions
Monosodium glutamate?(MSG) is a food additive and an environmental agent, that can affect inflammation.
Safety Profile
Moderately toxic by
intravenous route. Mildly toxic by ingestion
and other routes. An experimental
teratogen. Other experimental reproductive effects. Human systemic effects by ingestion
and intravenous routes: somnolence,
hallucinations and distorted perceptions,
headache, dyspnea, nausea or vomiting,
dermatitis. The cause of "Chnese restaurant
syndrome." When heated to decomposition
it emits toxic fumes of NOx and Na2O.
Safety
Monosodium glutamate is widely used in foods and oral
pharmaceutical formulations. It is generally regarded as moderately
toxic on ingestion or intravenous administration. Adverse effects
include somnolence, hallucinations and distorted perceptions,
headache, dyspnea, nausea or vomiting, and dermatitis. The lowest
lethal oral dose in humans is reported to be 43 mg/kg.The use of
monosodium glutamate in foods has been controversial due to the
so-called ‘Chinese Restaurant Syndrome’, although
it is generally regarded as safe at intake levels of up to 6 mg/kg bodyweight.In Europe, total glutamate intake from food ranges from
5–12 g/day.
There has been a report of a foreign body granuloma caused by
monosodium glutamate after a BCG vaccination.
Environmental Fate
MSG is a white, odorless powder with high water solubility. If
released into the air, it remains in the particulate phase until
removed by deposition.
storage
Aqueous solutions of monosodium glutamate may be sterilized by
autoclaving. Monosodium glutamate should be stored in a tight
container in a cool, dry place.
Toxicity evaluation
Although several mechanisms have been proposed to be
responsible for causing CRS, none has been extensively studied.
One hypothesis has been that the effects are due to an immediate
hypersensitivity reaction. Since no immunoglobulin E
(IgE)-mediated reaction has been documented, there is no
direct evidence that this is the case. Another hypothesis is that vitamin B6 deficiency plays a role in the response because the
symptoms were prevented by supplementing individuals with
the vitamin. Since glutamate can be converted to acetylcholine
by the tricarboxylic acid cycle, it has also been proposed that
the effects are due to an increase in acetylcholine levels. It has
been noted that after MSG ingestion, there is a decrease in the
levels of cholinesterase (the enzyme that breaks down acetylcholine).
Due to inadequate investigations, it is not currently
known if any or all of these mechanisms are responsible for
CRS. The neurotoxicity of MSG has only been demonstrated in
rodent species and rabbits after exposure to very large doses.
The neurotoxic effect has been attributed to excitotoxicity.
Regulatory Status
GRAS listed. Accepted in Europe for use as a food additive in
certain applications. Included in the FDA Inactive Ingredients
Database (oral syrup). Included in nonparenteral medicines licensed
in the UK. Included in subcutaneous vaccine injections.
Check Digit Verification of cas no
The CAS Registry Mumber 142-47-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 2 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 142-47:
(5*1)+(4*4)+(3*2)+(2*4)+(1*7)=42
42 % 10 = 2
So 142-47-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H9NO4.2Na/c6-3(5(9)10)1-2-4(7)8;;/h3H,1-2,6H2,(H,7,8)(H,9,10);;/q;2*+1/p-2
142-47-2Relevant articles and documents
Enzyme-Catalyzed Organic Synthesis: Electrochemical Regeneration of NAD(P)H from NAD(P) Using Methyl Viologen and Flavoenzymes
DiCosimo, Robert,Wong, Chi-Huey,Daniels, Lacy,Whitesides, George M.
, p. 4622 - 4623 (1981)
A procedure for enzyme-catalyzed organic synthesis is described in which regeneration of NAD(P)H from NAD(P) is accomplished by the electrochemical reduction of oxidized to reduced methyl viologen (MV2+ --> MV1+) followed by flavoenzyme-catalyzed reduction of the nicotinamide cofactor by this MV+1 (Scheme I).
CAGED COMPOUND, AND MANUFACTURING METHOD AND EXPRESSION METHOD OF CAGED COMPOUND
-
Paragraph 0166; 0167, (2019/03/01)
PROBLEM TO BE SOLVED: To provide a caged compound excellent in light reactivity and dark place stability, and capable of deprotection by a visible light. SOLUTION: A caged compound is represented by the following general formula (1). In the general formula (1), R1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cyano group, an alkoxy group, a hydroxy group, or an alkylamino group, R2 represents an alkyl group or a hetero atom other than a nitrogen atom, R3 represents a hydrogen atom, a halogen atom or an alkyl group, X represents a monovalent anion, Y represents a monovalent organic group, Z represents a hydrogen atom or a monovalent organic group, and a represents 0 or 1, however a represents 0 when R2 represents the hetero atom other than the nitrogen atom. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
Silicon nanowire photocathodes for light-driven electroenzymatic synthesis
Lee, Sahng Ha,Ryu, Gyeong Min,Nam, Dong Heon,Kim, Jae Hong,Park, Chan Beum
, p. 3007 - 3011 (2015/09/28)
The photoelectroenzymatic synthesis of chemical compounds employing platinum nanoparticle-decorated silicon nanowires (Pt-SiNWs) is presented. The Pt-SiNWs proved to be an efficient material for photoelectrochemical cofactor regeneration because the silicon nanowires absorbs a wide range of the solar spectrum while the platinum nanoparticle serve as an excellent catalyst for electron and proton transfer. By integrating the platform with redox enzymatic reaction, visible-light-driven electroenzymatic synthesis of L-glutamate was achieved. Compared to electrochemical and photochemical methods, this approach is free from side reactions caused by sacrificial electron donors and has the advantage of applying low potential to realize energy-efficient and sustainable synthesis of chemicals by a photoelectroenzymatic system.
Process for chemical reaction of amino acids and amides yielding selective conversion products
-
Page 7-8, (2008/06/13)
The invention relates to processes for converting amino acids and amides to desirable conversion products including pyrrolidines, pyrrolidinones, and other N-substituted products. L-glutamic acid and L-pyroglutamic acid provide general reaction pathways to numerous and valuable selective conversion products with varied potential industrial uses.
