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Hydroxy Acids Productionand Applications
Hydroxy Acids Productionand Applications
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1. INTRODUCTION
Hydroxy acids are organic acids having one or more hydroxyl group attached directly to the
carbon chain of an aliphatic or alicyclic carbon atom. Hydroxy acids occur in nature and can
also be synthesized through chemical or enzymatic methods. Many of the hydroxy acids occur
in plants i.e. sugar cane, tomatoes, oranges, lemons, grapes, apples, etc. and in animal tissues.
Since time immemorial, human civilization use many hydroxy acids in form of crude extracts
of plants and their various parts for curing many ailments and diseases. Ancient Sumarian and
Egyptian knew the analgesic property of willow leaf and use its extract for curing joint pain
and inflammation, now it is well known that it contain salicylic acid as an active ingredient
(Jack, 1997). There are many traditional preparations in ‘Ayurveda’ an ancient Indian science,
containing one or more hydroxy acids, used as antiaging, anti-inflammatory and for other skin
disorders (Datta et al., 2011). Formulations containing hydroxy acids have been used in clinical
practice for decades to treat a variety of skin infection. These acids have a broad range of
application in various fields e.g. cosmetics (Saint-Leger et al., 2007), pharmaceutical and food
processing (Kornhauser et al., 2010). In cosmetics hydroxy acids are used for the treatment of
various skin diseases such as in treating photoaging, acne, pigmentation disorders and psoriasis
(Wang, 1999; Kornhauser et al., 2010). Hydroxy acids have transformed skin care since their
introduction to dermatology (Van Scott & Yu, 1974; Green, 2006; Green et al., 2009). A range
of pharmaceutically important chiral synthons are being synthesized using hydroxy acids as
precursor, e.g. α-hydroxyphenylacetic acid (mandelic acid) used in the synthesis of antitumor
agents (Surivet & Vatele, 1999), antiobesity agents, semi synthetic penicillin (Furlenmeier et
al., 1976) and cephalosporin (Terreni et al., 2001). Hydroxy acids and their derivatives are
useful starting materials in synthetic organic chemistry and can be synthesized by biochemical
resolution of racemates and by asymmetric synthesis. Biochemical processes are preferred over
chemical processes as these allow ecofriendly synthesis with high chemo- and regio-selectivity
and yield. However, the information on synthesis of hydroxy acids through biological route is
scanty and only a few reports are available. In this chapter synthesis of hydroxy acids with a
focus on enzymatic routes and their applications are discussed.
Contd...
Caffeic acid C9H8O4 3-(3,4-Dihydroxyphenyl 2-propenoic acid
Salicylic acid C7H6O3 2-Hydroxybenzoic acid
m-Hydroxybenzoic acid C7H6O3 3-Hydroxybenzoic acid
p-Hydroxybenzoic acid C7H6O3 4-Hydroxybenzoic acid
Vanillic acid C8H8O4 4-Hydroxy-3-methoxybenzoic acid
Syringic acid C9H10O5 4-hydroxy-3,5-dimethoxybenzoic acid
Protocatechuic acid C7H6O4 3,4-Dihydroxybenzoic acid
Gentisic acid C7H6O4 2,5-Dihydroxybenzoic acid
Gallic acid C7H6O5 3,4,5-Trihydroxybenzoic acid
Phloroglucinol carboxylic acid C7H6O5 2,4,6-Trihydroxybenzoic acid
high temperature, pressure and produce a significant amount of by-products due to side reaction
caused by extreme reactivity of the resident hydroxyl oxygen (Miller and Peretti, 2001; Kirimura
et al., 2010).
Pseudomonas and Penicillium can be used for the production of α-HIB from acetone cyanohydrins
using nitrilase or nitrile hydrates/amidases (Fig. 11).
4.2.1.2.2 Biooxidation of tert-butanol: A biooxidation route for the synthesis of α-HIB by
bacterial degradation pathway of methyl tert-butyl ether (MTBE) via tert-butanol has been
reported (Lopes et al., 2008). In Mycobacterium austroafricanum IFP 2012, a none-heme alkane
monooxygenase is hydroxylating tert-butanol and resulting diol is further oxidized by two novel
dehydrogenases, designated as MpdB and MpdC, to the carboxylic acid. The enzyme system
for the oxidation of tert-butanol has also been described for the MTBE-degrading bacterial
strains Methylibium petroleiphilum PM1 (Hristova et al., 2007) and Aquincola tertiaricarbonis
L108 (Schafer et al., 2007).
4.2.1.3 Glycolic acid: Glycolic acid (GLA) is synthesized chemoenzymatically from glycolonitrile
(GLN) to ammonium glycolate, using a nitrilase derived from Acidovorax facilis 72W (Wu
et al., 2007) (Fig. 12). Ammonium glycolate is than subsequently converted to GLA by ion
exchange. Glycolic acid (GLA) and polyglycolic acid (PGA) are used in various industrial and
medical products.
Fig. 12: Chemoenzymatic synthesis of glycolic acid from formic acid and HCN.
Fig. 11: Production of -hydroxyisobutyric acid from acetoncyanohydrin via nitrilase or nitrile
hydratase/amidase mediated hydrolysis.
5.2 Medicine
Hydroxy acids have numerous applications in medical field. α-Hydroxy acid can be used to
improve the anti-inflammatory efficacy of cortisteroids. Polymer of α-hydroxyisobutyric acid
i.e., polymethyl methacrylate has a good degree of compatibility with human tissue, and can be
68 Advances in Industrial Biotechnology
Fig. 14: -HIB a precursor for the synthesis of various important compounds.
used for replacement intraocular lenses in the eye when the original lens has been removed in
the treatment of cataracts (Atchison, 1990; Khanna & Cernovsky, 2012). In orthopedic surgery,
PMMA bone cement is used to affix implants and to remodel lost bone (Khanna & Cernovsky
2012). α-Hydroxybutyrate is an early biomarker of insulin resistance and glucose intolerance
in a non-diabetic population (Gall et al., 2010).
(R)-(-)-Mandelic acid (R-MA) is an important chiral intermediate for the production
of pharmaceuticals such as semisynthetic penicillins, cephalosporins, antitumor agents, and
antiobesity agents (Tang et al., 2009). Mandelic acid condensation polymer act as a microbicide
against human immunodeficiency virus (HIV) and herps simplex virus (HSV) (Lourens et al.,
Hydroxy Acids: Production and Applications 69
2002). This polymer blocks the binding of HIV and HSV to cells by targeting the envelope
glycoprotein gp120 and gb2, respectively (Herold et al., 2002). Mandelic acid is also used as
urinary antiseptics. Mandelic acid with acid sodium phosphate as the acidifying agent, with
sodium bicarbonate is used for the treatment of urinary tract infection (Van Putten, 1979).
Benzilic acid derivatives have antihistamine and anesthetic properties (Forbes and Marshall,
1951). Phenyllactic acid (PLA) has been found in cultures of Lactobacillus plantarum that show
antifungal activity (Lavermicocca, 2003).
β-Hydroxypropanoic acid and their derivative hydrazides and thiosemicarbozides show anti-
inflammatory, analgesic and antimicrobial activity. β-Hydroxybutyric acid is used as an energy
source by the brain when blood glucose level is low.
γ-Hydroxybutyric acid (GBA) used as a neuroprotective therapeutic nutrient to treat cataplexy
and narcolepsy. Poly (hydroxyl) polymer can be used as scaffolds for tissue engineering or a
drug carrier for controlled drug delivery. Mechanism is based on the cleavage of the polymer
chain into smaller fragments by biodegradation and subsequent release of drug into the medium
(Wee et al., 2004). Biodegradable polymers from glycolide and lactide finds applications in
the controlled delivery of pharmaceuticals, such as hormones LHRH (Luteinizing hormone
releasing hormone), TRH (thyroid releasing hormone), calcitonin and various steroids (Asano
et al., 1989; Heya et al., 1991), antibiotics, including ampicillin, gentamicin, polymyxin B and
chloramphenicol (Benoit et al., 1997; Calhoun and Mader, 1997).
Salicylic acid is a well-known aromatic carboxylic acid used as a precursor for the production
of acetylsalicylic acid and the later is widely used as a non-steroidal anti-inflammatory drug i.e.
aspirin (Jack et al., 1997; Jeffreys, 2004). Salicylic acid itself is an antipyretic, anti-infammatory
and analgesic (Levy, 1981). Methyl salicylate is used as a liniment to soothe joint and muscle
pain, and choline salicylate is used topically to relieve the pain of aphthous ulcers, a type of
mouth ulcer.
5.4 Cosmetics
α-Hydroxy acids are one of the most powerful and most popular tools available in the skin
care industry. Mandelic acid has also long been known to have antibacterial properties, which
70 Advances in Industrial Biotechnology
are especially beneficial in the treatment of acne and oily skin. The side effects of mandelic
acid are minimal, especially when compared to similar skin care ingredients such as glycolic
acid (an alpha hydroxy acid) or hydroquinone (a skin lightening ingredient). Mandelic acid is
recommended in various skin diseases condition i.e., acne, melasma, wrinkles (Taylor, 1999).
The moisturizing property of lactic acid makes it ideal for treating dry skin (Narayanan et
al., 2004). Polymers of α-hydroxyisobutyric acid i.e. methacrylic acid has various application in
cosmetics. It is used to permanently raise indented scars and fill in folds like the nasolabial folds
(Clark, 1996).
Salicylic acid is known for its ability to ease aches and pains and reduce fevers. As with other
β-hydroxy acids, salicylic acid is a key ingredient in many skin-care products for the treatment
of Seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris and warts (Steele et
al., 1988). Because of its effect on skin cells, salicylic acid is used in several shampoos used
to treat dandruff. Parabens are a group homologous series of hydroxybenzoic acid, esterified at
the C-4 position (including methyl-, ethyl-, propyl-, butyl-, heptyl- and benzyl-paraben), used
singly or in combination to exert an antimicrobial effect and are present in approximately 80%
of cosmetics (Soni, 2005).
6. CONCLUSIONS
Hydroxy acids are important organic acids having one or more hydroxyl group. They are available
naturally as well as synthesized by different chemical and enzymatic reactions. These acids have
immense market potential and are used as cosmetics, drug or drug precursors, building blocks
in chemical synthesis, monomer of various biopolymers and bioplastics, drug delivery, tissue
engineering and production of various commodity chemicals. There are number of chemical
processes available for the synthesis of hydroxy acids, but have some serious disadvantages in
term of requirement of energy, harsh conditions, costly catalyst and formation of by-products,
often results in a threat to environment. Some of the hydroxy acids e.g., glycolic acid, mandelic
acid, p-hydroxybenzoic acid, α-hydroxyisobutyric acid, have been produced through enzymatic
72 Advances in Industrial Biotechnology
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