BETAİNE

Synonyms:
betaine; 107-43-7; glycine betaine; oxyneurine; lycine; Trimethylglycine; Abromine; Trimethylglycocoll; Glycocoll betaine; Glycylbetaine; Rubrine C; acidin-pepsin ; alpha-Earleine; Cystadane; Jortaine; N,N,N-trimethylglycine; Trimethylaminoacetic acid; Loramine AMB 13; 2-(trimethylazaniumyl)acetate; trimethylammonioacetate; Glycine, trimethylbetaine; BETAINE, ANHYDROUS; Betaine hydrochloride; (Trimethylammonio)acetate; Trimethylaminoacetate; Betafin; Methanaminium, 1-carboxy-N,N,N; trimethyl-, inner salt; 2-(Trimethylammonio)Acetate; Glykokollbetain [German]; Cocamidopropyl betaine; kokoamidpropil betain; Kokoamid Propil Betain; Amphoteric L; Softazoline LP; Obazoline CAB; Amphitol 20AB; Anpholex LB 2; Rewoteric AMB 12; Tego-Betain L 90; 4292-10-8; Lauroylamide propylbetaine; 3-Lauroylamidopropyl betaine; UNII-23D6XVI233; Dimethyl(lauramidopropyl)betaine; Lauroylaminopropyldimethylaminoacetate; N-Laurylamidopropyl-N,N-dimethylbetaine2-[3-(DODECANOYLAMINO)PROPYL-DIMETHYL-AMMONIO]ACETATE; Cocoamidopropyl betaine; 65277-51-2; 1-Propanaminium; N-(carboxymethyl)-N,N-dimethyl-3-[(1-oxododecyl)amino]-; inner salt; 1-Propanaminium; N-(carboxymethyl)-N,N-dimethyl- 3-[(1-oxododecyl)amino]-; hydroxide; inner salt; (3-(Lauroylamino)propyl)dimethylaminoacetic acid; [3-(Lauroylamino)propyl]dimethylaminoacetic acid; Amphosol LB; Obazoline LAB; Empigen BR; Lexaine LM; Monateric LMAB; 1-Propanaminium; N-(carboxymethyl)-N,N-dimethyl-3-((1-oxododecyl)amino)-; Mackam LMB; Softazoline LPB-R; Enagicol L 30B; Dehyton L 12; Rikabion B 300; Lauroylamidopropylbetaine; Lebon 2000L; AC1L2FXAC1Q22BQ; SCHEMBL22684; DTXSID4041282; CTK5C248; NSC8191; MolPort-023-220-314; (3-Lauramidopropyl)dimethylbetaine; 23D6XVI233; C19H38N2O3; NSC 8191; NSC-8191; EINECS 224-292-6; (3-Laurylaminopropyl)dimethylaminoacetic acid; hydroxide,inner salt; 61789-40-0; AN-20275; I427; LP010942; N,N-Dimethyl-N-dodecanoylaminopropylbetaine; Glycine; (3-lauramidopropyl)dimethylbetaine; FT-0670746; 2-[(3-Dodecanamidopropyl)dimethylaminio]acetate; N-(Dodecylamidopropyl)-N,N-dimethylammonium betaine; W-105096; 2-[3-(dodecanoylamino)propyl-dimethylazaniumyl]acetate; (3-Laurylaminopropyl)dimethylaminoacetic acid; UNII-5OCF3O11KX; MRUAUOIMASANKQ-UHFFFAOYSA-N; (Carboxymethyl)(3-lauramidopropyl)dimethylammonium Hydroxide Inner Salt,1-Propanaminium,N-dimethyl-3-[(1-oxododecyl)amino]-, hydroxide, inner salt; Ammonium (carboxymethyl)(3-lauramidopropyl)dimethyl-, hydroxide, inner salt; N-(Carboxymethyl)-N,N-dimethyl-3-[(1-oxododecyl)amino]-1-propanaminium Hydroxide Inner Salt; 1-Propanaminium, N-(carboxymethyl)-N,N-dimethyl-3-((1-oxododecyl)amino)-hydroxide,inner salt; 5437-10-5; N-(Carboxymethyl)-N,N-dimethyl-3-((1-oxododecyl)amino)-1-propanam- inium hydroxide, inner salt; cocamidopropyl betaine; cocamidopropylbetaine; KOKOAMİDOPROPİL BETAİN; KOKOAMIDOPROPIL BETAIN; KOKAMİDPROPİL BETAİN; KOKAMIDPROPIL BETAIN; Acidol; Methanaminium, 1-carboxy-N,N,N-trimethyl-, hydroxide, inner salt; Aminocoat; Greenstim; FinnStim; Glycine-Betaine; Betafin BP; betain; betayin; la betaine
 

Betaine

A betaine in chemistry is any neutral chemical compound with a positively charged cationic functional group such as a quaternary ammonium or phosphonium cation (generally: onium ions) that bears no hydrogen atom and with a negatively charged functional group such as a carboxylate group that may not be adjacent to the cationic site. A betaine is a specific type of zwitterion. Historically, the term was reserved for TMG (trimethylglycine) only. Biologically, TMG is involved in methylation reactions and detoxification of homocysteine.

The pronunciation of the compound reflects its origin and first isolation from sugar beets (Beta vulgaris subsp. vulgaris), and does not derive from the Greek letter beta (β), however, it often is pronounced beta-INE or BEE-tayn.[1]

In biological systems, many naturally occurring betaines serve as organic osmolytes. These are substances synthesized or taken up from the environment by cells for protection against osmotic stress, drought, high salinity, or high temperature. Intracellular accumulation of betaines permits water retention in cells, thus protecting from the effects of dehydration. This accumulation is non-perturbing to enzyme function, protein structure, and membrane integrity. Betaine is also a methyl donor of increasingly recognised significance in biology.

Glycine betaine

The chemical structure of trimethylglycine
Main article: Trimethylglycine
The original betaine, N,N,N-trimethylglycine, was named after its discovery in sugar beet (Beta vulgaris subsp. vulgaris) in the nineteenth century.[2] It is a small N-trimethylated amino acid. It is a zwitterion, which cannot isomerize because there is no labile hydrogen atom attached to the nitrogen atom. This substance may be called glycine betaine to distinguish it from other betaines.

Commercial uses
Phosphonium betaines are intermediates in the Wittig reaction.

The addition of betaine to polymerase chain reactions improves the amplification of DNA by reducing the formation of secondary structure in GC-rich regions. The addition of betaine has been reported to enhance the specificity of the polymerase chain reaction by eliminating the base pair composition dependence of DNA melting.[3][4]

See also
Cocamidopropyl betaine
Mesoionic
Mesomeric betaine
Osmoprotectants
Ylide

Molecular Weight of Betaine:    117.15 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3-AA of Betaine:    0.5    Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Countof Betaine:    0    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count of Betaine:    2    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of Betaine:    1    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass of Betaine:    117.078979 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass of Betaine:    117.078979 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area of Betaine:    40.1 Ų    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of Betaine:    8    Computed by PubChem
Formal Chargeof Betaine:    0    Computed by PubChem
Complexity of Betaine:    87.6    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Countof Betaine:    0    Computed by PubChem
Defined Atom Stereocenter Count of Betaine:    0    Computed by PubChem
Undefined Atom Stereocenter Count of Betaine:    0    Computed by PubChem
Defined Bond Stereocenter Count    of Betaine:0    Computed by PubChem
Undefined Bond Stereocenter Count of Betaine:    0    Computed by PubChem
Covalently-Bonded Unit Count of Betaine:    1    Computed by PubChem
Compound of Betaine Is Canonicalized    Yes

Betaine is a modified amino acid consisting of glycine with three methyl groups that serves as a methyl donor in several metabolic pathways and is used to treat the rare genetic causes of homocystinuria. Betaine has had only limited clinical use, but has not been linked to instances of serum enzyme elevations during therapy or to clinically apparent liver injury.

Betaine Hydrochloride is the hydrochloride form of betaine, a crystalline alkaloid occurring in sugar beets and other plants. Betaine, acting as a transmethylating metabolic intermediate, is the oxidation product of choline. Betaine hydrochloride is used as a gastric acidifier supplement.

Glycine betaine is the amino acid betaine derived from glycine. It has a role as a fundamental metabolite. It is an amino-acid betaine and a glycine derivative. It is a conjugate base of a N,N,N-trimethylglycinium.

Cocamidopropyl betaine (CAPB) is a chemical compound found in many personal care and household cleaning products. CAPB is a surfactant, which means that it interacts with water, making the molecules slippery so they don`t stick together.
When water molecules don`t stick together, they are more likely to bond with dirt and oil so when you rinse away the cleaning product, the dirt rinses away, too. In some products, CAPB is the ingredient that makes lather.
Cocamidopropyl betaine is a synthetic fatty acid made from coconuts, so products that are considered "natural" can contain this chemical. Still, some products with this ingredient may cause unpleasant side effects.
Cocamidopropyl betaine allergic reaction
Some people have an allergic reaction when they use products containing CAPB. In 2004, the American Contact Dermatitis Society declared CAPB the "Allergen of the Year."
Since then, a 2012 scientific review of studies found that it`s not the CAPB itself that causes an allergic reaction, but two impurities that are produced in the manufacturing process.
The two irritants are aminoamide (AA) and 3-dimethylaminopropylamine (DMAPA). In multiple studies, when people were exposed to CAPB that did not contain these two impurities, they did not have an allergic reaction. Higher grades of CAPB that have been purified don`t contain AA and DMAPA and don`t cause allergic sensitivities.
Skin discomfort
If your skin is sensitive to products that contain CAPB, you may notice tightness, redness, or itchiness after you use the product. This kind of reaction is known as contact dermatitis. If the dermatitis is severe, you may have blisters or sores where the product came into contact with your skin.
Most of the time, an allergic skin reaction like this will heal on its own, or when you stop using the irritating product or use an over-the-counter hydrocortisone cream.
If the rash doesn`t get better in a few days, or if it is located near your eyes or mouth, see a doctor.
Eye irritation
CAPB is in several products intended for use in your eyes, like contact solutions, or it`s in products that may run into your eyes as you shower. If you are sensitive to the impurities in CAPB, your eyes or eyelids could experience:
pain, redness, itchiness, swelling
If rinsing the product away does not take care of the irritation, you may want to see a doctor.
Products with cocamidopropyl betaine
CAPB can be found in facial, body, and hair products like: shampoos, conditioners, makeup removers,liquid soaps,body wash,shaving cream,contact lens solutions,gynecological or anal wipes,some toothpastes
CAPB is also a common ingredient in household spray cleaners and cleaning or disinfecting wipes.How to tell if a product has cocamidopropyl betaine
CAPB will be listed on the ingredient label. The Environmental Working Group lists alternative names for CAPB, including:1-propanaminium hydroxide inner salt
In cleaning products, you may see CAPB listed as:
CADG, cocamidopropyl dimethyl glycine, disodium cocoamphodipropionate
The National Institute of Health maintains a Household Product Database where you can check to see if a product you use may contain CAPB.Cocamidopropyl betaine (CAPB) and coconut diethanolamide (CDEA), which are manufactured from coconut oil, are widely used as chemical substances with surfactant property in shampoo, liquid soap and skin cleaners. Allergic contact dermatitis (ACD) may occur against these substances, especially cocamidopropyl betaine. ACD developing against these two substances is rarely seen in the literature. Here we reported a case of ACD caused by CABP and CDEA which admitted with complaints of redness,peeling and cracking of hands.
Occupational allergic contact dermatitis due to cocamidopropyl betaine and coconut diethanolamide

Cocamidopropyl betaine (CAPB) and coconut diethanolamide (CDEA), which are manufactured from coconut oil, are widely used as chemical substances with surfactant property in shampoo, liquid soap and skin cleaners. Allergic contact dermatitis (ACD) may occur against these substances, especially cocamidopropyl betaine. ACD developing against these two substances is rarely seen in the literature. Here we reported a case of ACD caused by CABP and CDEA which admitted with complaints of redness,peeling and cracking of hands.
Concern    Reference
Violation of industry recommendations - Restricted in cosmetics; use, concentration, or manufacturing restrictions - Unsafe in products left on skin and not rinsed off    Cosmetic Ingredient Review Assessments
Recommended restricted in cosmetics - use, concentration, or manufacturing restrictions - any    Cosmetics Ingredient Review (CIR) 2010. Tentative Report: Cocamidopropyl Betaine and Related Amidopropyl Betains as used in Cosmetics. Pink Book 4, August 30-31, 2010.
Determined safe for use in cosmetics, subject to concentration or use limitations - Safe for use in cosmetics with some qualifications Cosmetic Ingredient Review Assessments
Cocamidopropyl betaine.
Abstract
Cocamidopropyl betaine (CAPB) is an amphoteric synthetic detergent that has been increasingly used in cosmetics and personal hygiene products (eg, shampoos, contact lens solutions, toothpaste detergents, makeup removers, bath gels, skin care products, cleansers, liquid soaps, antiseptics, and gynecologic and anal hygiene products) because it induces relatively mild skin irritation. Delayed T-cell-mediated type IV hypersensitivity reactions to CAPB have been reported, and contact sensitization prevalence is estimated at between 3.0 and 7.2%. The increasing rates of sensitization led to CAPB`s being named Allergen of the Year in 2004. Related impurities rendered during the manufacturing process (such as amidoamine and dimethylaminopropylamine) are thought to play a role in sensitization.
 

Names
IUPAC name
{[3-(Dodecanoylamino)propyl](dimethyl)ammonio}acetate
Other names
2-[(3-Dodecanamidopropyl)dimethylaminio]acetate
Identifiers
CAS Number:61789-40-0 
ECHA InfoCard:100.057.308
EC Number:263-058-8
PubChem CID:20280
Properties:
    Chemical formula:C19H38N2O3
    Molar mass:342.524 g·mol−1

Cocamidopropyl betaine (CAPB) is a mixture of closely related organic compounds derived from coconut oil and dimethylaminopropylamine.[1] CAPB is available as a viscous pale yellow solution and it is used as a surfactant in personal care products. The name reflects that the major part of the molecule, the lauric acid group, is derived from coconut oil. Cocamidopropyl betaine to a significant degree has replaced cocamide DEA.

Production
Despite the name cocamidopropyl betaine is not synthesized from betaine. Instead it is produced in a two step manner, beginning with the reaction of dimethylaminopropylamine (DMAPA) with fatty acids from coconut or palm kernel oil (lauric acid, or its methyl ester, is the main constituent). The primary amine in DMAPA is more reactive than the tertiary amine, leading to its selective addition to form an amide. In the second step chloroacetic acid reacts with the remaining tertiary amine to form a quaternary ammonium center (a quaternization reaction).[2]

CH3(CH2)10COOH + H2NCH2CH2CH2N(CH3)2 → CH3(CH2)10CONHCH2CH2CH2N(CH3)2
CH3(CH2)10CONHCH2CH2CH2N(CH3)2 + ClCH2CO2H + NaOH → CH3(CH2)10CONHCH2CH2CH2N+(CH3)2CH2CO2− + NaCl + H2O
Chemistry
CAPB is a fatty acid amide containing a long hydrocarbon chain at one end and a polar group at the other. This allows CAPB to act as a surfactant and as a detergent. It is a zwitterion, consisting of both a quaternary ammonium cation and a carboxylate.

Specifications and properties
Cocamidopropyl betaine is used as a foam booster in shampoos.[3] It is a medium-strength surfactant also used in bath products like hand soaps. It is also used in cosmetics as an emulsifying agent and thickener, and to reduce irritation purely ionic surfactants would cause. It also serves as an antistatic agent in hair conditioners, which most often does not irritate skin or mucous membranes. However, some studies indicate it is an allergen.[4][5][6]

CAPB is obtained as an aqueous solution in concentrations of about 30%.

Typical impurities of leading manufacturers today:

Sodium monochloroacetate < 5 ppm
Amidoamine (AA) < 0.3%
Dimethylaminopropylamine (DMAPA) < 15 ppm
Glycerol < 3%
The impurities AA and DMAPA are most critical, as they have been shown to be responsible for skin sensitization reactions. These by-products can be avoided by a moderate excess chloroacetate and the exact adjustment of pH value during betainization reaction accompanied by regular analytical control.