MANDELIC ACID

Mandelic Acid = Vanillin

CAS Number : 90-64-2 
EC Number :  202-007-6
PubChem CID : 1292
ChemSpider ID : 388690
Chemical formula :  C8H8O3
Molar mass    : 152.149 g·mol−1
Density            : 1.30 g/cm3
Melting point    : 119 °C 
Boiling point    : 321.8 °C

Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. 
Mandelic acid is a white crystalline solid that is soluble in water and polar organic solvents. 
Mandelic acid is a useful precursor to various drugs. 
The molecule of Mandelic acid is chiral. 
The racemic mixture is known as paramandelic acid.

Isolation, synthesis, occurrence of Mandelic Acid
Mandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler (1801–1868) while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. The name is derived from the German "Mandel" for "almond".

Mandelic acid is usually prepared by the acid-catalysed hydrolysis of mandelonitrile,which is the cyanohydrin of benzaldehyde. 
Mandelonitrile can also be prepared by reacting benzaldehyde with sodium bisulfite to give the corresponding adduct, forming mandelonitrile with sodium cyanide, which is hydrolyzed.
Alternatively, it can be prepared by base hydrolysis of phenylchloroacetic acid as well as dibromacetophenone.
It also arises by heating phenylglyoxal with alkalis.

Biosynthesis of Mandelic Acid
Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway. 
Mandelate racemase interconverts the two enantiomers via a pathway that involves cleavage of the alpha-CH bond. 
Mandelate dehydrogenase is yet another enzyme on this pathway.
Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated.
Phenylpyruvic acid is another precursor to mandelic acid.

Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase. 
The biotechnological production of 4-hydroxy-mandelic acid and mandelic acid on the basis of glucose was demonstrated with a genetically modified yeast Saccharomyces cerevisiae, in which the hydroxymandelate synthase naturally occurring in the bacterium Amycolatopsis was incorporated into a wild-type strain of yeast, partially altered by the exchange of a gene sequence and expressed.

Mandelic acid also arises from the biodegradation of styrene, as detected in urine.

Uses of Mandelic Acid
Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections.
Mandelic acid has also been used as an oral antibiotic, and as a component of chemical face peels analogous to other alpha hydroxy acids.
The drugs cyclandelate and homatropine are esters of mandelic acid.

Mandelic acid is a 2-hydroxy monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are substituted by phenyl and hydroxyl groups. 
Mandelic acid has a role as an antibacterial agent and a human xenobiotic metabolite. 
Mandelic acid is a 2-hydroxy monocarboxylic acid and a member of benzenes. 
Mandelic acid derives from an acetic acid. 
Mandelic acid is a conjugate acid of a mandelate.

Mandelic acid is an approved aromatic, alpha hydroxy acid. 
Mandelic acid is used as an ingredient in cosmetics and drug products applied topically.
Mandelic acid is a natural product found in Aloe africana, Achillea millefolium, and other organisms with data available.

Sources/Uses of Mandelic Acid
Used as a urinary antiseptic; [Merck Index] Has been used as a urinary antiseptic, oral antibiotic, and component of chemical face peels.
-antimicrobial        
-biocide

Mandelic acid is a type of gentle alpha hydroxy acid (AHA). 
Mandelic acid may help reduce acne, fine lines, and wrinkles and improve the appearance of uneven skin.
Mandelic acid is a type of AHA, which people use in skin care routines as chemical peels or exfoliants. 
The substance derives from bitter almonds.

Many cosmetic companies describe mandelic acid as a gentle AHA, so it may be suitable for people with sensitive skin or those who find other chemical exfoliants too strong for their skin.
In comparison with other AHAs, mandelic acid is a large molecule, about twice the size of glycolic acid. 
Mandelic acid also penetrates the skin much more slowly. 
This slow absorption may mean that it feels less irritating to the skin than other AHAs.

Benefits of Mandelic Acid
Mandelic acid offers a wide range of benefits for the skin. 
However, further conclusive research into mandelic acid is necessary to identify its properties and potential benefits.
Mandelic acid may be gentler than other AHAs and suitable for use by people of all skin types, especially those with sensitive and acne-prone skin.
Like other AHAs, mandelic acid loosens the bonds that adhere the dead or old skin cells to the skin surface. 
This helps shed old, dryer skin cells to reveal new smoother skin cells.

In the process of chemical exfoliation, mandelic skin eliminates damaged and older skin cells and replaces them with newer, firmer skin cells. 
Mandelic acid may help the skin appear firmer and more elastic, reducing the appearance of wrinkles and fine lines.
Mandelic acid may help unclog pores, dissolve blackheads and comedones, and control sebum production.

Mandelic acid has antibacterial properties and may help remove acne-causing bacteria in the skin. 
Mandelic acid may also reduce inflammation and redness, which helps reduce the occurrence of breakouts, including cystic acne breakouts.
Mandelic acid may be suitable for people with sensitive skin. 
Skin experts believe it has fewer side effects and irritates the skin less than other AHAs.
However, a person should consider doing a patch test before trying mandelic acid for the first time. 

People should also make sure that they use safe concentrations and sufficient intervals between applications.
A person should consider speaking with a doctor or dermatologist before adding mandelic acid to their skin routine. 
Dermatologists can assess a person’s skin better, recommend the best products according to their skin type, and educate them on proper use.

Hydroxy acids have been used throughout history in various forms to promote a radiant and healthy complexion, long before the chemical structure or even their existence was known. 
Egyptian women took baths in sour milk in order to improve their skin. 
French women in the court of Louis XIV washed their faces with old wine for the same reasons. 
Old fashioned facial masks made from fruit, honey or yogurt were also unknowingly taking advantage of “fruit acids” as their active ingredients.

Part of the alpha hydroxy acid family, mandelic acid, named after the German mandel (almond), is derived from the hydrolysis of bitter almonds. 
Like other AHAs, mandelic acid is suitable for treating a huge array of prevalent skin care concerns, such as photo-ageing, rosacea, irregular pigmentation, inflammatory noncystic acne and blackheads. 
But unlike its more aggressive equivalents, mandelic acid does not result in skin irritation, erythema and burning.

Its potent yet remarkably gentle action is attributed to the relatively large molecular weight, when compared to other AHAs, which slows down epidermal penetration and results in more even exfoliation with less irritation. 
This enables individuals, who cannot normally tolerate high concentrations of AHAs to benefit from the range of advantages that AHAs offer. 
Mandelic acid is the only AHA that also exhibits the same action as BHA, due to its ability to clean inside the pore, it helps to remove blockages of sebum and dead skin cells that can lead to blackheads. 

Apart from this highly valuable cosmeceutical activity, mandelic acid also demonstrates well-documented antiseptic activity, which makes it especially suitable for hypersensitive acne-prone skin types. 
In fact, mandelic acid was initially examined in open clinical trials with regard to its antibacterial properties. 
It was soon discovered that sustained and continuous use of mandelic acid can radically diminish fine lines and wrinkles in a similar way as glycolic acid does.

Mandelic acid is an alpha hydroxy acid (AHA) derived from bitter almonds, but is more gentle than some of the other AHAs like glycolic acid and lactic acid. 
AHAs work by exfoliating the layers of dead skin away by breaking the bonds between cells to reveal brighter, clearer skin as well as help to clear pores and create a more even tone.

Mandelic acid is a go-to anti-ageing ingredient in the world of skincare. 
Mandelic acid works to accelerate cell turnover by dissolving the tiny bonds that hold skin cells together, helping to remove dead skin on the surface that can lead to dull complexions, as well as fine lines. 
Mandelic acid also strengthens collagen, one of the building blocks of the skin’s support network that gives it youthful firmness.

Mandelic acid’s antibacterial properties are extremely helpful in treating acne. 
Mandelic acid also helps to regulate sebum production and in turn decrease the occurrence of breakouts. 
Mandelic acid has even been shown to benefit those who suffer from cystic acne.

Benefits of Mandelic Acid
Exfoliates: Mandelic acid is a chemical exfoliant, meaning it removes layers of older skin cells through a reaction with the skin (rather than exfoliating via abrasive scrubs).
Promotes cell turnover: By releasing skin cells attached to the surface of the skin, mandelic acid works to increase cell turnover, reducing the appearance of skin damage or acne.
Brightens skin: Exfoliated skin appears brighter and mandelic acid goes a step further, strengthening the skin so it stays bright with continued use.
Reduces hyperpigmentation: Increased cell turnover and exfoliating properties mean the acid reduces the look of dark marks and sun damage.

Mandelic acid is an alpha hydroxyl acid derived from bitter almonds but is less irritating to the skin compared to Glycolic acid. 
Mandelic acid has a larger molecular weight that sits on the surface of the skin and gently exfoliates without irritating the skin. 
Mandelic acid helps to exfoliate dead skin cells and promotes skin cell turnover, lightens blemishes and dark spots, fights skin ageing and results in brighter, even-toned and healthier, radiant skin. 
Additional key ingredients like Panthenol, Centella Asiatica Extract and Beta-Glucan soothes and moisturizes the skin even after exfoliation.

Mandelic acid is an aromatic AHA with the molecular formula C8H8O3. 
Mandelic acid is a white crystalline solid that is soluble in water and most common organic solvents.
Mandelic acid has a long history of use in the medical community as an antibacterial agent, particularly in the treatment of urinary tract infections. 
It has also been used as an oral antibiotic. 
Lately, mandelic acid has gained popularity as a topical skin care treatment for adult acne. 

Mandelic acid is also used as an alternative to glycolic acid in skin care products. 
Mandelic acid is a larger molecule than glycolic acid, which makes it better tolerated on the skin. 
Mandelic acid is also advantageous in that it possesses antibacterial properties, whereas glycolic acid does not.

Its use as a skin care modality was pioneered by James E. Fulton, who helped develop retinoic acid in 1969 with his mentor, Albert Kligman, at the University of Pennsylvania. 
On the basis of this research, dermatologists now suggest mandelic acid as an appropriate treatment for a wide variety of skin pathologies, from acne to wrinkles; it is especially good in the treatment of adult acne because it addresses both of these concerns. 
Mandelic acid is also recommended as a prelaser and postlaser resurfacing treatment, reducing the amount and length of irritation.

Mandelic acid peels are commercialized nowadays as gels with a specific viscosity, which make them user friendly for beginners.
Mandelic acid is a large-molecule alpha-hydroxy acid with slow epidermal penetration. 
Similar to the other alpha-hydroxy acids described, Mandelic acid decreases corneocyte adhesion and is keratolytic. 
Aside from acne treatment,Mandelic acid is often used for skin rejuvenation and lightening. 
Mandelic acid can be combined with SA for the treatment of acne vulgaris. 

Application of Mandelic Acid
Racemic mandelic acid in the form of mandelates is generally used as a pharmaceutical component due to its analgesic, antirheumatic, and spasmolytic effects. 
It undergoes resolution to form (+)- and (-)-enantiomers that are widely used as chiral resolving agents in enantioseparation of various other racemates via salt formation.

Mandelic acid is an optically active crystalline hydroxy acid C8H8O3 that is obtainable in the levorotatory D-form from amygdalin by hydrolysis but is usually made in the racemic form by reaction of benzaldehyde with hydrocyanic acid and then hydrochloric acid and that is used chiefly in the form of its salts as a bacteriostatic agent for genitourinary tract infections.

Mandelic acid is a type of alpha hydroxy acid (AHA) that’s derived from bitter almonds. 
Mandelic acid is a powerful ingredient which can help to supercharge your skincare routine when it needs a boost. 
Like other types of AHAs it works by exfoliating the skin. 
Mandelic acid is gentler compared to glycolic acid because its molecule size is twice as big, so it takes longer to penetrate the skin and is therefore less likely to cause irritation.
Finally, like all acids, mandelic has the tendency to make skin sensitive to UVA rays, so wearing an SPF during the day is non-negotiable if you want to keep hold of your glow. 

Mandelic acid can be used to treat three major skin concerns: signs of ageing, acne and enlarged pores, as well as pigmentation that is the result of excess sun exposure, acne scarring, taking hormonal contraceptives and pregnancy. 
Mandelic acid targets these concerns by speeding up cell turnover that slows with age.

Mandelic acid belongs to the alpha hydroxy acid (AHA) family. 
Extracted from bitter almonds, this naturally derived acid has been shown to improve all skin types from oily and acne prone to mature, sensitive and everything in between. 
Best known for its exfoliation capability, mandelic acid is gentler than its fellow AHAs, glycolic and lactic acids. 
Plus, it's oil soluble which allows it to not only exfoliate the surface of your skin but work deeper down on your pores as well.

The natural acid boosts skin cell turnover by dissolving the tiny bonds that hold skin cells together. 
This sloughs away the dull, dead cells to reveal the smooth, healthy ones underneath. 
An excellent choice for exfoliation beginners, mandelic acid provides a gentle experience. 
The larger size mandelic molecule absorbs more slowly than other AHAs, meaning it won't cause irritation, even to sensitive skin.

Widely used as an anti-aging treatment, mandelic acid provides a multitude of benefits ranging from lightening discoloration and signs of hyperpigmentation to softening lines and wrinkles and treating acne. 
When added to skin care, mandelic acid accelerates cell turnover to strengthen collagen and reverse damage caused from aging and sun exposure. 
It also helps to regulate sebum production to prevent future blemishes. 
Find the solution that's right for your skin in the curated shop below.

Mandelic acid is an alpha hydroxy acid (AHA) extracted from bitter almond that has been studied extensively as a treatment for common skin concerns as photoaging, acne and melasma. 
Mandelic acid use was developed by the doctor behind Retin-A and found to be extremely effective for adult acne due to its unique anti ageing properties and unique antibacterial properties. 
Mandelic acid can be used by individuals with rosacea, active acne cysts and pimples. 
Despite being stronger, it is less irritating than glycolic acid and can be used safely on dark skin. 

This makes Mandelic Acid the top choice for anyone looking to enjoy the benefits of Alpha Hydroxy Acid skincare. 
We have formulated a range of mandelic acid products, to suit a wide variety of skin types. 
Our popular mandelic acid cleanser is a great place to start your mandelic acid skincare journey, combining mandelic acid with poly hydroxy acid in the form of a gentle face wash. 
We also offer a gentle 5% mandlic acid lotion, and mandelic acid serums with prebiotics and glycoin.

Substance identity

EC / List no.: 202-007-6
CAS no.: 90-64-2
Mol. formula: C8H8O3

Hazard classification & labelling of Mandelic Acid
Danger! According to the classification provided by companies to ECHA in REACH registrations this substance causes serious eye damage.

About Mandelic Acid
Mandelic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 to < 10 tonnes per annum.
Mandelic acid is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.

Consumer Uses of Mandelic Acid
Mandelic acid is used in the following products: cosmetics and personal care products.
Other release to the environment of Mandelic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).

Article service life of Mandelic Acid
Other release to the environment of Mandelic acid is likely to occur from: indoor use in long-life materials with high release rate (e.g. release from fabrics, textiles during washing, removal of indoor paints).
Mandelic acid can be found in products with material based on: paper used for articles with intense direct dermal (skin) contact during normal use such as personal hygiene articles (e.g. nappies, feminine hygiene products, adult incontinence products, tissues, towels, toilet paper).

Widespread uses by professional workers of Mandelic Acid
Mandelic acid is used in the following products: laboratory chemicals and pH regulators and water treatment products.
Mandelic acid is used in the following areas: health services and scientific research and development.
Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).

Formulation or re-packing of Mandelic Acid
Mandelic acid is used in the following products: cosmetics and personal care products and laboratory chemicals.
Mandelic acid has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of Mandelic acid can occur from industrial use: formulation of mixtures.

Uses at industrial sites of Mandelic Acid
Mandelic acid is used in the following products: laboratory chemicals and pH regulators and water treatment products.
Mandelic acid is used in the following areas: health services and scientific research and development.
Mandelic acid is used for the manufacture of: chemicals.
Release to the environment of Mandelic acid can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid and in the production of articles.

Manufacture of Mandelic Acid
ECHA has no public registered data on the routes by which Mandelic acid is most likely to be released to the environment.

Synonyms:
Mandelic acid
mandelic acid
Benzeneacetic acid, .alpha.-hydroxy-
(2S)-2-hydroxy-2-phenylacetic acid
2-hydroxy-2-phenylacetic acid
DL-Mandelic acid
hydroxy(phenyl)acetic acid
hydroxy(phenyl)acetic acid; α-Hydroxybenzeneacetic acid
Mandelic Acid
Mandelic acid
mandelic acid
15769-78-5
611-72-3
71036-61-8
90-64-2
MANDELIC ACID
dl-Mandelic acid
2-hydroxy-2-phenylacetic acid
90-64-2
611-72-3
Phenylglycolic acid
Amygdalic acid
Almond acid
Paramandelic acid
Racemic mandelic acid
Uromaline
p-Mandelic acid
(RS)-Mandelic acid
2-Phenylglycolic acid
Hydroxy(phenyl)acetic acid
Phenylhydroxyacetic acid
Glycolic acid, phenyl-
Kyselina mandlova
2-Phenyl-2-hydroxyacetic acid
DL-Hydroxy(phenyl)acetic acid
(+/-)-mandelic acid
2-hydroxy-2-phenyl-acetic acid
Benzeneacetic acid, alpha-hydroxy-
NSC 7925
Benzeneacetic acid, .alpha.-hydroxy-
alpha-Hydroxyphenylacetic acid
alpha-Hydroxy-alpha-toluic acid
Kyselina 2-fenyl-2-hydroxyethanova
(+/-)-alpha-Hydroxyphenylacetic acid
.alpha.-Hydroxyphenylacetic acid
CHEBI:35825
(+-)-alpha-Hydroxybenzeneacetic acid
NSC-7925
alpha-Hydroxybenzeneacetic acid
.alpha.-Hydroxy-.alpha.-toluic acid
.alpha.-Toluic acid, .alpha.-hydroxy-
Ammonium mandelate
(+)-Mandelate, XXI
Acido mandelico
(+-)-Mandelic acid
Benzeneacetic acid, alpha-hydroxy-, homopolymer
Benzeneacetic acid, .alpha.-hydroxy-, (.+/-.)-
mandelic-acid
2-Hydroy-2-phenylacetic acid
Mandelic acid [USP]
DL-Amygdalic Acid
DL-Mandelicacid
Acido mandelico [Italian]
DL-2-Hydroxy-2-phenylacetic acid
Kyselina mandlova [Czech]
32518-00-6
(+-)-2-Hydroxy-2-phenylethanoic acid
alpha-Toluic acid, alpha-hydroxy-
(+-)-alpha-Hydroxyphenylacetic acid
EINECS 202-007-6
EINECS 210-277-1
2-Hydroxy-2-phenylethanoic acid
acidomandelico
alpha-Hydroxybenzeneacetic acid, (+-)-
AI3-06293
Kyselina 2-fenyl-2-hydroxyethanova [Czech]
Benzoglycolic acid
Phenylacetic acid, alpha-hydroxy-
NCGC00166022-01
l(+)mandelic acid
(+) mandelic acid
(+)-mandelic acid
PPCM
SAMMA
hyroxyphenylacetic acid
Pregabalin Impurity C
(+/-)-alpha-Hydroxybenzeneacetic acid
Mandelic acid, 99%
(-)-Mandelate, XX
hydroxyphenyl acetic acid
81432-25-9
Pregabalin EP Impurity C
WLN: QYR&VQ
hydroxy-phenyl-acetic acid
Mandelic acid, >=99%
DL-Mandelic acid, 99%
SCHEMBL1050
(.+/-.)-Mandelic acid
CHEMBL1609
(+)-Phenylhydroxyacetic acid
(?)-Phenylhydroxyacetic acid
2-Hydroxy-2-phenylaceticacid
MLS001074208
.alpha.-Phenylhydroxyacetic acid
DTXSID6023234
BDBM92715
NSC7925
Mandelic acid condensation polymer
2-oxidanyl-2-phenyl-ethanoic acid
HMS2230F19
HMS3371M20
HMS3373A03
(2rs)-hydroxy(phenyl)ethanoic acid
BBL028097
MFCD00064250
s3363
STL283951
AKOS000118795
AKOS016050628
CS-W016307
DB13218
HY-W015591
KS-1423
LS00073
MCULE-3206518139
NCGC00166023-01
NCGC00166269-01
(.+/-.)-alpha-Hydroxybenzeneacetic acid
AC-12228
SMR000653543
SY001645
SY001670
DB-016128
DB-016158
DS-000887
AM20060842
FT-0600010
FT-0601504
FT-0625487
FT-0628148
M0038
W7345
Benzeneacetic acid, .alpha.-hydroxy-, ( )-
Benzeneacetic acid, .alpha.-hydroxy-, (S)-
A19434
DL-Mandelic acid, analytical reference material
MLS-0090887.0001
A833072
AE-562/40233036
Q412293
Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.R)-
(2RS)-2-Hydroxy-2-phenylacetic Acid (Mandelic Acid)
Mandelic Acid ((2RS)-2-Hydroxy-2-phenylacetic Acid)
14A53E4A-8315-42A7-9D60-DE06CCBB1AF9
F2191-0202
Z955123532
Mandelic acid, United States Pharmacopeia (USP) Reference Standard
Mandelic acid; (2RS)-2-Hydroxy-2-phenylacetic acid ; ?-Hydroxy-Benzeneacetic acid;