E 270

CAS number: 50-21-5
EC number: 200-018-0
Molecular formula: C3H6O3

E 270 is a hydroxycarboxylic acid CH3CH(OH)COOH with two stereoisomers (D(-) and L(+)) and E 270 has several applications in food, chemical, pharmaceutical and health care industries. 
E 270 is primarily used for food and pharmaceutical applications, preferentially the L(+) isomer, since E 270 is the only lactic acid isomer produced in the human body. 

Around 20 to 30% of the lactic acid production is used to obtain biopolymers (polylactic acid). 
Other uses of E 270 include fibers and green solvents.

E 270 is fully commercially available and largely (90%) produced by bacteria through anaerobic fermentation of sugars. 
E 270 can also be commercially produced by chemical synthesis. 

The chemical production pathway gives an optical inactive racemic mixture (with the same quantity of L and D isomers), while the anaerobic fermentation pathway mostly yieldsone of the two stereoisomers, depending on the microorganism chosen. 
The biotechnological option is widely available due to E 270 renewable origin. 
E 270 can be produced via fermentation of sugars from different biomass, such as: starch crops, sugar crops, lignocellulosic materials and also from whey (a residue from cheese production). 

E 270 is an organic acid occurring naturally in the human body and in fermented foods. 
E 270 is used in a wide range of food, beverages, personal care, healthcare, cleaners, feed & pet food and chemical products as a mild acidity regulator with flavour enhancing and antibacterial properties. 

The commercial production of E 270 is typically done by fermentation. 
Because the L(+) form is preferred for E 270 better metabolisation, Jungbunzlauer has chosen to produce pure L(+)-lactic acid by traditional fermentation of natural carbohydrates.

L(+)-lactic acid is a colourless to yellowish, nearly odourless, syrupy liquid with a mild acid taste. 
E 270 is commercially available as aqueous solutions of various concentrations. 

These solutions are stable under normal storage conditions.
E 270 is non-toxic to humans and the environment, but concentrated solutions of lactic acid can cause skin irritation and eye damage. 
E 270 is readily biodegradable.

E 270, also called lactic acid, was discovered in 1780 by Swedish chemist, Carl Wilhelm Scheele, who isolated the lactic acid from sour milk as an impure brown syrup and gave E 270 a name based on its origins: 'Mjölksyra'. 
The French scientist Frémy produced lactic acid by fermentation and this gave rise to industrial production in 1881.
E 270 is produced by the fermentation of sugar and water or by chemical process and is commercially usually sold as a liquid.

Pure and anhydrous racemic lactic acid (E 270) is a white crystalline solid with a low melting point. 
E 270 has two optical forms, L(+) and D(-). 
E 270 is the biological isomer as E 270 is naturally present in the human body.

E 270 (lactic acid) comes in both R (D-) and S (L+) enantiomers which can be manufactured individually to near perfect optical purity. 
This means E 270 is great in the production of other products which require a specific stereochemistry.

E 270 is used frequently in the cosmetic industry due to the effect of promoting collagen production, helping to firm the skin against wrinkles and sagging. 
E 270 can also cause micro peeling, which can help reduce various scars and age spots. 
E 270 is a great solution for people with sensitive or dry skin where exfoliants don’t work.

E 270 is used as a food preservative, curing agent, and flavoring agent. 
E 270 is an ingredient in processed foods and is used as a decontaminant during meat processing. 
E 270 is produced commercially by fermentation of carbohydrates such as glucose, sucrose, or lactose, or by chemical synthesis.

E 270, also named ‘milk acid’, is an organic acid with the following chemicalformula: CH3CH(OH)CO2H. 
The official name given by the International Union ofPure and Applied Chemistry (IUPAC) is 2-hydroxypropanoic acid. 

E 270 can be naturally produced, but E 270 importanceis correlated with synthetic productions. 
Pure E 270 is a colourless andhydroscopic liquid.
Lactic acid can be defined a weak acid because of E 270 partial dissociationin water and the correlated acid dissociation constant (Ka= 1.38 - 10−4).

E 270 is a chiral compound with a carbon chain composed of a central (chiral) atomand two terminal carbon atoms. 
A hydroxyl group is attached to the chiral carbon atom while oneof the terminal carbon atoms is part of the carboxylic group and the other atom is part of the methylgroup. 
Consequently, two optically active isomeric forms of lactic acid exist: L(+) form, alsonamed (S)-lactic acid, and D(−) form, or (R)-lactic acid. L(+)-lactic acid is the biological isomer.

E 270 is an organic acid. 
E 270 has a molecular formula CH3CH(OH)COOH. 

E 270 is white in the solid state and E 270 is miscible with water.
When in the dissolved state, E 270 forms a colorless solution. 

Production includes both artificial synthesis as well as natural sources. 
E 270 is an alpha-hydroxy acid (AHA) due to the presence of a hydroxyl group adjacent to the carboxyl group. 

E 270 is used as a synthetic intermediate in many organic synthesis industries and in various biochemical industries. 
The conjugate base of lactic acid is called lactate.

In solution, E 270 can ionize, producing the lactate ion CH3CH(OH)CO−2. 
Compared to acetic acid, E 270s pKa is 1 unit less, meaning lactic acid is ten times more acidic than acetic acid. 
This higher acidity is the consequence of the intramolecular hydrogen bonding between the α-hydroxyl and the carboxylate group.

E 270 is chiral, consisting of two enantiomers. 
One is known as l-(+)-lactic acid or (S)-lactic acid and the other, E 270 mirror image, is d-(−)-lactic acid or (R)-lactic acid. 

A mixture of the two in equal amounts is called dl-lactic acid, or racemic lactic acid. Lactic acid is hygroscopic. 
dl-Lactic acid is miscible with water and with ethanol above E 270 melting point, which is around 16, 17 or 18 °C. 

d-Lactic acid and l-lactic acid have a higher melting point. 
Lactic acid produced by fermentation of milk is often racemic, although certain species of bacteria produce solely (R)-lactic acid. 
On the other hand, lactic acid produced by anaerobic respiration in animal muscles has the (S) configuration and is sometimes called "sarcolactic" acid, from the Greek "sarx" for flesh.

Antibacterial mechanism of E 270 on physiological and morphological properties of Salmonella Enteritidis, Escherichia coli and Listeria monocytogenes:
Pathogens could be completely inactivated after exposure to E 270.
E 270 resulted in great leakage of protein of three pathogens.

Bacterial protein bands of E 270-treated cells got fainter or disappeared.
Z-Average sizes of pathogens were changed to smaller after E 270 treatment.
E 270 caused collapsed or even broken cells with obvious pits and gaps.

E 270 is widely used to inhibit the growth of important microbial pathogens, but E 270 antibacterial mechanism is not yet fully understood. 
The objective of this study was to investigate the antibacterial mechanism of lactic acid on Salmonella Enteritidis, Escherichia coli and Listeria monocytogenes by size measurement, TEM, and SDS-PAGE analysis. 

The results indicated that 0.5% lactic acid could completely inhibit the growth of Salmonella Enteritidis, E. coli and L. monocytogenes cells. 
Meanwhile, E 270 resulted in leakage of proteins of Salmonella, E. coli and Listeria cells, and the amount of leakage after 6 h exposure were up to 11.36, 11.76 and 16.29 μg/mL, respectively. 

Fifty strains each of Staphylococcus aureus, beta haemolytic Streptococci, Proteus species, Esch coli and Pseudomonas aeruginosa were subjected to 2%, 1 % and 0. 1 % lactic acid in peptorie water. 
Minimum inhibitory concentration of E 270 for all the strains of each of these organisms was 0.1% or 1%. 

Depending upon E 270's concentration, E 270 added to peptone water brings down the PH to 2.5-4 which by itself has some inhibitory effect on the microorganisms. 
E 270 however, retains E 270 inhibitory effect even if the Ph of the peptone water is brought back to 7.3. 

E 270 is a nontoxic and non-sensitizing agent because E 270 is a normal metabolite of the body. 
Thus, E 270 can be used as a safe and effective antibacterial agent for local application.

Applications of E 270:
Due to the high hygroscopicity of E 270, E 270 concentrated aqueous solutions are usually used - syrupy, colorless, odorless liquids. 
Oxidation of E 270 is usually accompanied by decomposition. 

Under the action of HNO 3 or O 2 of air in the presence of Cu or Fe, HCOOH, CH 3 COOH, (COOH) 2 , CH 3 CHO, CO 2 and pyruvic acid are formed. 
Reduction of E 270 HI leads to propionic acid, and reduction in the presence of Re-mobile leads to propylene glycol.

E 270 dehydrates to acrylic acid, when heated with HBr, forms 2-bromopropionic acid, when the Ca salt reacts with PCl 5 or SOCl 2 -2-chloropropionyl chloride . 
In the presence of mineral acids, self-esterification of E 270 occurs with the formation of lactone, as well as linear polyesters. 

When E 270 interacts with alcohols, hydroxy acids RCH 2 CH (OH) COOH are formed, and when lactic acid salts react with alcohol esters. 
The salts and esters of E 270 are called lactates.

E 270 is formed as a result of lactic acid fermentation (with sour milk, sauerkraut, pickling vegetables, ripening cheese, ensiling feed)
D- lactic acid is found in tissues of animals, plants, and also in microorganisms.

In industry, E 270 is obtained by hydrolysis of 2-chloropropionic acid and E 270 salts (100 ° C) or lactonitrile CH 3 CH (OH) CN (100 ° C, H 2 SO 4 ), followed by the formation of esters, the isolation and hydrolysis of which leads to a high quality. 
Other methods of producing E 270 are known: the oxidation of propylene with nitrogen oxides (15-20 ° C) followed by treatment with H 2 SO 4 , the interaction of CH 3 CHO with CO (200 ° C, 20 MPa).

E 270 is used in the food industry, in mordant dyeing, in leather production, in fermentation shops as a bactericidal agent, for the production of medicines, plasticizers. 
Ethyl and butyl lactates are used as solvents for cellulose ethers, drying oils, vegetable oils; butyl lactate - as well as a solvent for some synthetic polymers.

In animals, l-lactate is constantly produced from pyruvate via the enzyme lactate dehydrogenase (LDH) in a process of fermentation during normal metabolism and exercise.
E 270 does not increase in concentration until the rate of lactate production exceeds the rate of lactate removal, which is governed by a number of factors, including monocarboxylate transporters, concentration and isoform of LDH, and oxidative capacity of tissues.

The concentration of blood lactate is usually 1–2 mM at rest, but can rise to over 20 mM during intense exertion and as high as 25 mM afterward.
In addition to other biological roles, l-lactic acid is the primary endogenous agonist of hydroxycarboxylic acid receptor 1 (HCA1), which is a Gi/o-coupled G protein-coupled receptor (GPCR).

In industry, E 270 fermentation is performed by lactic acid bacteria, which convert simple carbohydrates such as glucose, sucrose, or galactose to lactic acid. 
These bacteria can also grow in the mouth; the acid they produce is responsible for the tooth decay known as caries.

In medicine, lactate is one of the main components of lactated Ringer's solution and Hartmann's solution. 
These intravenous fluids consist of sodium and potassium cations along with lactate and chloride anions in solution with distilled water, generally in concentrations isotonic with human blood. 
E 270 is most commonly used for fluid resuscitation after blood loss due to trauma, surgery, or burns.

Uses of E 270:
A normal intermediate in the fermentation (oxidation, metabolism) of sugar. 
The concentrated form is used internally to prevent gastrointestinal fermentation.
Conversion to glucose via gluconeogenesis in the liver and release back into the circulation

E 270 in Food:
E 270 is naturally present in many foodstuffs. 
E 270 is formed by natural fermentation in products such as cheese, yogurt, soy sauce, sourdough, meat products and pickled vegetables.

E 270 is also used in a wide range of food applications such as bakery products, beverages, meat products, confectionery, dairy products, salads, dressings, ready meals, etc. 
E 270 in food products usually serves as either as a pH regulator or as a preservative. 
E 270 is also used as a flavoring agent.

In Meat, Poultry & Fish of E 270:
E 270 can be used in meat, poultry and fish in the form of sodium or potassium lactate to extend shelf life, control pathogenic bacteria (improve food safety), enhance and protect meat flavor, improve water binding capacity and reduce sodium.

In Beverages of E 270:
Because of E 270 mild taste, E 270 is used as an acidity regulator in beverages such as soft drinks and fruit juices.

In Pickled vegetables of E 270:
E 270 is effective in preventing the spoilage of olives, gherkins, pearl onions and other vegetables preserved in brine.

In Salads & dressings of E 270:
E 270 may be also used as a preservative in salads and dressings, resulting in products with a milder flavor while maintaining microbial stability and safety.

In Confectionery of E 270:
Formulating hard-boiled candy, fruit gums and other confectionery products with E 270 results in a mild acid taste, improved quality, reduced stickiness and longer shelf life.

In Dairy of E 270:
The natural presence of lactic acid in dairy products, combined with the dairy flavor and good antimicrobial action of E 270, makes lactic acid an excellent acidification agent for many dairy products.

In Baked Goods of E 270:
E 270 is a natural sourdough acid, which gives the bread E 270 characteristic flavor, and therefore E 270 can be used for direct acidification in the production of sourdough.

In Savory Flavors of E 270:
E 270 is used to enhance a broad range of savory flavors. 
E 270s natural occurrence in meat and dairy products makes lactic acid an attractive way to enhance savory flavors.

In Pharmaceutical of E 270:
The primary functions for the pharmaceutical applications are: pH-regulation, metal sequestration, chiral intermediate and as a natural body constituent in pharmaceutical products.

In Biomaterials of E 270:
E 270 is a valuable component in biomaterials such as resorbable screws, sutures and medical devices.

In Detergents of E 270:
E 270 well known for its descaling properties and is widely applied in household cleaning products. 
Also, E 270 is used as a natural anti-bacterial agent in disinfecting products.

In Technical of E 270:
E 270 is used in a wide variety of industrial processes where acidity is required and where E 270 properties offer specific benefits. 
Examples are the manufacture of leather and textile products and computer disks, as well as car coating.

In Animal Feed of E 270:
E 270 is a commonly used additive in animal nutrition. 
E 270 has health promoting properties, thus enhancing the performance of farm animals. 
E 270 can be used as an additive in food and/or drinking water.

E 270 in biodegradable plastics
E 270 is the principal building block for Poly Lactic Acid (PLA). 
PLA is a biobased and bio-degradable polymer that can be used for producing renewable and compostable plastics.

Manufacturing of E 270:
E 270 can be produced naturally or synthetically. 
Commercial E 270 is produced naturally by fermentation of carbohydrates such as glucose, sucrose, or lactose. 

With the addition of lime or chalk of E 270, the raw materials are fermented in a fermenter and crude calcium lactate is formed. 
The gypsum is separated from the crude calcium lactate, which results in crude E 270. 
The crude E 270 is purified and concentrated and L(+) lactic acid is the result.

E 270, is an organic acid with applications in beer production as well as the cosmetic, pharmaceutical, food and chemical industries. 
E 270 is commonly used as a preservative and antioxidant. 
E 270 also has uses as a fuel additive, chemical intermediate, acidity regulator, and disinfectant.

One specific use of E 270 is in I.V solutions, where Lactic acid is an electrolyte to help replenish the bodies fluids. 
E 270 is also used in dialysis solutions, which results in a lower incidence of side effects compared to Sodium Acetate which can also be used.

Production of E 270:
E 270 is produced industrially by bacterial fermentation of carbohydrates, or by chemical synthesis from acetaldehyde.
In 2009, E 270 was produced predominantly (70–90%) by fermentation. 

Production of racemic lactic acid consisting of a 1:1 mixture of d and l stereoisomers, or of mixtures with up to 99.9% l-lactic acid, is possible by microbial fermentation. 
Industrial scale production of d-lactic acid by fermentation is possible, but much more challenging.

As a starting material for industrial production of E 270, almost any carbohydrate source containing C5 and C6 sugars can be used. 
Pure sucrose, glucose from starch, raw sugar, and beet juice are frequently used.
E 270 producing bacteria can be divided in two classes: homofermentative bacteria like Lactobacillus casei and Lactococcus lactis, producing two moles of lactate from one mole of glucose, and heterofermentative species producing one mole of lactate from one mole of glucose as well as carbon dioxide and acetic acid/ethanol.

Chemical production of E 270:
Racemic E 270 is synthesized industrially by reacting acetaldehyde with hydrogen cyanide and hydrolysing the resultant lactonitrile. 
When hydrolysis is performed by hydrochloric acid, ammonium chloride forms as a by-product; the Japanese company Musashino is one of the last big manufacturers of lactic acid by this route.
Synthesis of both racemic and enantiopure E 270s is also possible from other starting materials (vinyl acetate, glycerol, etc.) by application of catalytic procedures.

Biology of E 270:
l-Lactic acid is the primary endogenous agonist of hydroxycarboxylic acid receptor 1 (HCA1), a Gi/o-coupled G protein-coupled receptor (GPCR).

Exercise and lactate:
During power exercises such as sprinting, when the rate of demand for energy is high, glucose is broken down and oxidized to pyruvate, and lactate is then produced from the pyruvate faster than the body can process E 270, causing lactate concentrations to rise. 
The production of lactate is beneficial for NAD+ regeneration (pyruvate is reduced to lactate while NADH is oxidized to NAD+), which is used up in oxidation of glyceraldehyde 3-phosphate during production of pyruvate from glucose, and this ensures that energy production is maintained and exercise can continue. 
During intense exercise, the respiratory chain cannot keep up with the amount of hydrogen ions that join to form NADH, and cannot regenerate NAD+ quickly enough.

The resulting lactate can be used in two ways:
Oxidation back to pyruvate by well-oxygenated muscle cells, heart cells, and brain cells
Pyruvate is then directly used to fuel the Krebs cycle

Conversion to glucose via gluconeogenesis in the liver and release back into circulation.
If blood glucose concentrations are high, the glucose can be used to build up the liver's glycogen stores.

However, lactate is continually formed even at rest and during moderate exercise. 
Some causes of this are metabolism in red blood cells that lack mitochondria, and limitations resulting from the enzyme activity that occurs in muscle fibers having high glycolytic capacity.

In 2004, Robergs et al. maintained that lactic acidosis during exercise is a "construct" or myth, pointing out that part of the H+ comes from ATP hydrolysis (ATP4− + H2O → ADP3− + HPO2− 4 + H+), and that reducing pyruvate to lactate (pyruvate− + NADH + H+ → lactate− + NAD+) actually consumes H+.

Lindinger et al. countered that they had ignored the causative factors of the increase in [H+]. 
After all, the production of lactate− from a neutral molecule must increase [H+] to maintain electroneutrality. 

The point of Robergs's paper, however, was that lactate− is produced from pyruvate−, which has the same charge. 
E 270 is pyruvate− production from neutral glucose that generates H+:

C6H12O6 + 2 NAD+ + 2 ADP3− + 2 HPO2−4  →  2 CH3COCO−2 + 2 H+ + 2 NADH + 2 ATP4− + 2 H2O
Subsequent lactate− production absorbs these protons:
2 CH3COCO−2 + 2 H+ + 2 NADH  →  2 CH3CH(OH)CO−2 + 2 NAD+

Overall:
C6H12O6 + 2 NAD+ + 2 ADP3− + 2 HPO2−4  →  2 CH3COCO−2 + 2 H+ + 2 NADH + 2 ATP4− + 2 H2O→  2 CH3CH(OH)CO−2 + 2 NAD+ + 2 ATP4 − + 2 H2O
Although the reaction glucose → 2 lactate− + 2 H+ releases two H+ when viewed on E 270 own, the H+ are absorbed in the production of ATP. 

On the other hand, the absorbed acidity is released during subsequent hydrolysis of ATP: ATP4− + H2O → ADP3− + HPO2−4 + H+. 
So once the use of ATP is included, the overall reaction is C6H12O6 → 2 CH3COCO−2 + 2 H+ .
The generation of CO2 during respiration also causes an increase in [H+].

History of E 270:
Swedish chemist Carl Wilhelm Scheele was the first person to isolate E 270 in 1780 from sour milk.
The name reflects the lact- combining form derived from the Latin word lac, which means milk. 

In 1808, Jöns Jacob Berzelius discovered that lactic acid (actually l-lactate) also is produced in muscles during exertion.
E 270s structure was established by Johannes Wislicenus in 1873.

In 1856, the role of Lactobacillus in the synthesis of E 270 was discovered by Louis Pasteur. 
This pathway was used commercially by the German pharmacy Boehringer Ingelheim in 1895.
In 2006, global production of lactic acid reached 275,000 tonnes with an average annual growth of 10%.

Synonyms of E 270:
2-Hydroxypropanoic acid
Lactic acid
1-Hydroxyethanecarboxylic acid
Ethylidenelactic acid
alpha-Hydroxypropionic Acid
Milchsäure (Dutch)
ácido lactico (Spanish)
Aacide lactique (French)
(RS)-2-Hydroxypropionsaeure
1-Hydroxyethanecarboxylic acid
2-Hydroxypropanoic acid
2-Hydroxypropionic acid
Acidum lacticum
Aethylidenmilchsaeure
DL-Lactic acid
DL-Milchsaeure
Ethylidenelactic acid
Kyselina 2-hydroxypropanova
Kyselina mlecna
Lactate
Lactic acid, dl-
Lactic acid (natural)
Lactic acid USP
Lactovagan
Milchsaeure
Milchsaure
Milk acid
Ordinary lactic acid
Propanoic acid, 2-hydroxy-
Propel
Propionic acid, 2-hydroxy-
Racemic lactic acid
SY-83
Tonsillosan
alpha-Hydroxypropionic acid
2- Hydroxy propanoic acid
2-HYDROXY-PROPANOIC ACID
2-hydroxy-propanoic acid
2-Hydroxypropanoic Acid
2-Hydroxypropanoic acid
2-hydroxypropanoic acid
2-Hydroxypropionic acid
2-hydroxypropionic acid
D-LACTIC ACID
DL-Lactic Acid
dl-lactic acid
LACTIC ACID
Lactic Acid
Lactic acid
lactic acid
Lactic acid
lactic acid
Milchsäure
Propanoic acid, 2-hydroxy-
Propanoic acid,2-hydroxy-
Tejsav
2-hydroxypropanoic acid
Lactic acid
2 Hydroxypropanoic Acid
2 Hydroxypropionic Acid
2-Hydroxypropanoic Acid
2-Hydroxypropionic Acid
Ammonium Lactate
D Lactic Acid
D-Lactic Acid
L Lactic Acid
L-Lactic Acid
Lactate
Lactate, Ammonium
Lactic Acid
Propanoic Acid, 2-Hydroxy-, (2R)-
Propanoic Acid, 2-Hydroxy-, (2S)-
Sarcolactic Acid
2-hydroxypropanoic acid
DL-Lactic acid
50-21-5
2-hydroxypropionic acid
Milk acid
Polylactic acid
lactate
Ethylidenelactic acid
Lactovagan
Tonsillosan
Racemic lactic acid
Propanoic acid, 2-hydroxy-
Ordinary lactic acid
Milchsaeure
Acidum lacticum
Kyselina mlecna
DL-Milchsaeure
Lactic acid USP
1-Hydroxyethanecarboxylic acid
Aethylidenmilchsaeure
alpha-Hydroxypropionic acid
Lacticacid
Lactic acid (natural)
FEMA No. 2611
26100-51-6
Kyselina 2-hydroxypropanova
Milchsaure [German]
Propionic acid, 2-hydroxy-
598-82-3
(RS)-2-Hydroxypropionsaeure
CCRIS 2951
HSDB 800
(+-)-2-Hydroxypropanoic acid
FEMA Number 2611
Kyselina mlecna
propanoic acid, hydroxy-
SY-83
DL- lactic acid
Propel
NSC 367919
AI3-03130
Purac FCC 80
Purac FCC 88
Kyselina 2-hydroxypropanova
EINECS 200-018-0
EINECS 209-954-4
MFCD00004520
EPA Pesticide Chemical Code 128929
BRN 5238667
(R)-2-Hydroxy-propionic acid;H-D-Lac-OH
CHEBI:78320
Poly(lactic acid)
C3H6O3
NSC-367919
NCGC00090972-01
2-hydroxy-propionic acid
DL-Lactic acid, 90%
E 270
DSSTox_CID_3192
(+/-)-Lactic acid
alpha-Hydroxypropanoic acid
C01432
DSSTox_RID_76915
DSSTox_GSID_23192
Milchsaure
Polactide
Lacticum acidum
D(-)-lactic acid
Cheongin samrakhan
UNII-3B8D35Y7S4
CAS-50-21-5
Cheongin Haewoohwan
Cheongin Haejanghwan
Lactic acid
lactasol
Propanoic acid, 2-hydroxy-, homopolymer
1-Hydroxyethane 1-carboxylic acid
Biolac