Chemical and Physical Behavior of Human HairBearbeitet vonClarence R. Robbins1. Auflage 2012. Buch. XXIII, 724 S. HardcoverISBN 978 3 642 25610 3Format (B x L): 15,5 x 23,5 cmGewicht: 1280 gWeitere Fachgebiete Medizin Klinische und Innere Medizin DermatologieZu Inhaltsverzeichnisschnell und portofrei erhältlich beiDie Online-Fachbuchhandlung beck-shop.de ist spezialisiert auf Fachbücher, insbesondere Recht, Steuern und Wirtschaft.Im Sortiment finden Sie alle Medien (Bücher, Zeitschriften, CDs, eBooks, etc.) aller Verlage. Ergänzt wird das Programmdurch Services wie Neuerscheinungsdienst oder Zusammenstellungen von Büchern zu Sonderpreisen. Der Shop führt mehrals 8 Millionen Produkte.
Chapter 2Chemical Composition of Different Hair TypesAbstract Human hair consists of proteins, lipids, water, trace elements andpigments. The composition of the first four of these components is the focus ofthis Chapter. About two decades ago the emphasis on the proteins of hair was on itsamino acid constituents which provided important information on the relativeamounts of different functional groups in different types of hair and in differentregions of the fiber. However, as a result of advances in the characterization andclassification of the different proteins and genes of keratins and keratin associatedproteins the focus today is on the proteins themselves. Several important newcontributions to the composition of the surface layers of hair and the proteins ofthe cell membrane complex have been and are continuing and therefore aresummarized in this Chapter. The current state of changes in the amino acids,proteins and lipids of hair by morphological region (including KAP and keratinproteins and where they reside), chemical and sunlight damage, diet, puberty andmenopause, and other factors have been and are being made and are summarizedhere. An expanded section on metals in hair, where in the fiber these metals resideand the functional groups that they bind to and their effects on hair chemistry,toxicity and disorders are included.2.1IntroductionSeveral important new and relatively recent contributions to the structure of the cellmembrane complex, the composition of the surface layers of hair, the overallstructure of the hair fiber and its follicle have been added to this Chapter. Recentstudies revealed details about endogenous and exogenous hair lipids and the criticalinvolvement of proteins and free lipids in the surface layers of hair including lipidcontributions to the protective properties of the cuticle and the isoelectric point.Advances in the classification and characterization of the different proteins andgenes involved in keratin and keratin associated proteins in human hair aresummarized in this Chapter and the analysis of protein fragments from hairC.R. Robbins, Chemical and Physical Behavior of Human Hair,DOI 10.1007/978-3-642-25611-0 2, # Springer-Verlag Berlin Heidelberg 2012105
1062 Chemical Composition of Different Hair Typesdamaged by cosmetic chemicals is a new and exciting area for future research. Theeffects of menopause on changes in the lipids of scalp hair have been added to thisChapter and the recently found effects of menopause on the diameter of hair fibershave been added to Chap. 9.Human hair is a complex tissue consisting of several morphological components(see Chap. 1), and each component consists of several different chemical types .Hair is an integrated system in terms of its structure and its chemical and physicalbehavior wherein its components can act separately or as a unit. For example, thefrictional behavior of hair is related primarily to the cuticle, yet, the cuticle, thecortex and its intercellular components act in concert to determine the softness ofhair. The tensile behavior of human hair is determined largely by the cortex, yet wehave learned that the physical integrity of the fiber to combing and grooming forcesis also affected by the non-keratin components of the cuticle and the cell membranecomplex. Nevertheless, for simplicity and ease of discussion, the different types ofchemicals that comprise human hair are generally described separately in thisChapter.Depending on its moisture content (up to 32% by weight), human hair, consistsof approximately 65% to 95% proteins. Proteins are condensation polymers ofamino acids. The structures of those amino acids that are found in human hair aredepicted in Table 2.1. Because of the large number of chemical reactions thathuman hair is subjected to by permanent waves, chemical bleaches, alkalinestraighteners and sunlight exposure, many of the proteins are fragmented andseveral of these amino acids are converted to amino acid derivatives depicted inTable 2.2. The remaining constituents are water, lipids (structural and free), pigment, and trace elements that are generally not free, but combined chemically withside chains of protein groups or with fatty-acid groups of sorbed or bound lipid.These different components of hair: proteins, lipids, water and trace elements aredescribed separately in this Chapter while pigments are described in more detail inChap. 5.Studies of the proteinaceous matter of human hair may be classified according tothe following types of investigation:Studies of individual or several amino acids,Analysis of types of amino acids,Fractionation and peptide analysis,Expression of genes, using in situ hybridization or reverse transcriptase-polymerase chain reaction (RT-PCR) expression by hair follicles or the use ofspecific protein antibodies or related techniques.Most studies of individual amino acids of keratin fibers involve the amino acidscystine or tryptophan. Quantitation of cystine can be accomplished by chemicalanalysis of mercaptan with [2, 3] or without hydrolysis  or spectrophotometrically on intact hair [5, 6]. With increasing sophistication in instrumental analysis,ESCA, SIMS, and different absorbance, reflectance and fluorescence techniques,spectrophotometric analysis on intact hair is becoming increasingly important.
2.1 Introduction107Chemical analyses for tryptophan have been described by Block and Bolling and are all hydrolytic procedures.McMillen and Jachowicz  based on prior work in the wool industry analyzedtryptophan and its kynurenine reaction products by fluorescence spectroscopy usingexcitation wavelengths of 290, 320 and 350 nm which provides emission bands at345, 420 and 465 nm. The emission band with a maximum at 345 nm corresponds toTryptophan with an absorption maximum at about 360 nm. The emission peak at465 nm from excitation at 320 and 350 nm matches the emission band of 1kynurenine which has an absorption maximum at about 360 nm. The emissionmaximum at 420 nm was ascribed to N-Formylkynurenine and has an absorptionTable 2.1 Structures of amino acids found in hydrolyzates from human hair (molecular weightsof these amino acids are listed in brackets)Aliphatic Hydrocarbon R GroupNH 3CO 2 Glycine CH 3 NH 3Alanine CO 2 NH 3Valine CO 2 NH 3Isoleucine  CO 2NH 3Leucine CO 2Aromatic Hydrocarbon R group NH 3Phenylalanine CO 2 NH 3Tyrosine CO 2OH
1082 Chemical Composition of Different Hair TypesDiacidic Amino AcidsCO2Lysine NH2NH3 CO2HNNH3 NHArginine NH2CO2 NH2NH3Ornithine CO2NNH3Histidine  NHCO2 HNNH3OCitrulline NH2Diacidic Amino AcidsCO2 CO2HNH3Aspartic Acid CO2 CO2HNH3Glutamic Acid Hydroxyl containing amino acidsCO2 OHNH3Threonine CH3 CO2NH3Serine OH
2.1 Introduction109Sulfur containing amino acids CO2SNH3 NH3SCO2Cystine CO2 NH3 SCH3Methionine CO2SHNH3 Cysteine CO2NH3SO3HCysteic Acid Heterocyclic amino acids in hairProline NH 2CO 2 NH 3CO 2NHTryptophan Aspartic acid and glutamic acids exist as the primary amides and the free acids in human hairmaximum at 320 nm. In this paper on thermal degradation of hair, the authorsclaimed that the spectra after thermal exposure indicate a decrease in the emissionintensities of all bands, probably related to thermal decomposition of thecorresponding chromophores. The largest reduction in the emission intensity isevident for the band at 345 nm corresponding to Tryptophan providing evidence forits photochemical degradation.Quantitative determination of several amino acids in human hair becameincreasingly widespread years ago following the development of the ion exchangechromatographic systems of Moore and Stein . But more recently, protein
1102 Chemical Composition of Different Hair TypesTable 2.2 Structure of amino acid degradation/derivative products found in human hairaDerivatives of cystineCystine oxidation products from peroxide bleaching–CH–CH2–S–SO–CH2–CH– cystine monoxide–CH–CH2–S–SO2–CH2–CH– cystine dioxide–CH–CH2–SO3M cysteic acid saltFrom sulfite perms and sunlight oxidation–CH–CH2–S–SO3M Bunte saltFrom TGA perms–CH–CH2–S–S–CH2–CO2MFrom GMT (OH)–CH2–OHHydrolysis gives the derivative above from TGA permsFrom cysteamine perms–CH–CH2–S–S–CH2–CH2–NH2*HXFrom strong alkalinity as (straighteners, perms, bleaches)–CH–CH2–S–CH2–CH– lanthionine–CH–CH2–NH–(CH2)4–CH– lysinoalanineDerivatives of amino acids other than cystineFrom strong alkalies (hydrolysis of rom chemical oxidation–CH–CH2–CH2–SO2–CH3 methionine sulfone (sulfoxide not demonstrated)From TGA perms–CH–(CH2)4–NH–CO–CH2–SH thioacetylated lysineFrom sunlight oxidation–CO–CO–R alpha keto derivatives and cross-links of these with amino groupsaDegradation of other amino acids such as tryptophan, lysine and histidine are known to occurfrom sun exposure, however, identification of the degradation products has not been madesequencing techniques such as the use of Polymerase chain reaction (PCR) primers,or analysis of cDNA’s with sequences that code specific proteins or even digestionto specific peptides and analysis by mass spectrometry or the use of specific proteinantibodies or other techniques have become increasingly important. Studies ofamino acid types are also used today, but less frequently. These involve determination of a specific functional group where more than one amino acid contains thattype of group such as, the titration of basic groups  and of acidic groups .Fractionation and peptide analysis is concerned primarily with fractionation intosimilar peptide types or even fractionation into the different morphologicalcomponents. Major areas of hair research concerned with the chemical compositionof hair and wool fibers, over the last two decades, have involved proteomics or thedetermination of the total proteins present in a fraction or region of the hair. Thisdefinition has been extended by some to include determining the proteins from
2.2 The Amino Acids and Proteins of Different Types of Hair111which fractions are derived from chemical degradation of hair by perming, oxidation and straightening reactions. Several important papers have been publisheddefining and classifying the types of proteins in human hair fibers. An initialclassification of hair proteins was described by Powell and G.E. Rogers. Importantadditions to this work have been reviewed in papers by M.A. Rogers and Langbeinet al. that are described in detail and referenced in Chap. 1 as well as in this Chapterin the section entitled, Major Protein Fractions of Hair. In addition, the structure,composition and degradation of the cuticle, the cortex and medulla, the cellmembrane complex and the composition of structural hair lipids are the majorfocus of this Chapter.2.2The Amino Acids and Proteins of Different Types of Hair2.2.1Whole-Fiber Amino Acid StudiesMore than three decades ago, a large number of investigations were described onthe analysis of the amino acids of whole human hair fibers. Whole-fiber amino acidanalysis has several limitations, because it provides average values for the aminoacid contents of the average proteinaceous substances of the fibers. Therefore, forwhole-fiber results, cross-sectional and axial differences in the composition of thefibers are averaged.A second complicating factor is hydrolytic decomposition of certain aminoacids. The most commonly used medium for keratin fiber hydrolysis is 5–6 Nhydrochloric acid. In studies involving acid hydrolysis of keratins, partial decomposition has been reported for cystine, threonine, tyrosine , phenylalanine, andarginine  with virtually complete destruction of tryptophan .With the above limitations in mind, the following discussion describes severalimportant factors contributing to differences in the whole-fiber amino acid analysisresults of human hair, reported in the literature.22.214.171.124Unaltered or “Virgin” Human HairUnaltered human hair is hair that has not been chemically modified by treatmentwith bleaches, permanent waves, straighteners, or hair dyes. Numerous publications[7, 13–28] describe results of the amino acid analysis of unaltered human hair.Table 2.1 depicts the structures for 22 amino acids that have been identified inhuman hair. Cysteic acid and other amino acids, derived from those amino acids ofTable 2.1, are also present in either weathered or cosmetically altered hair, seeTable 2.2. Table 2.3 summarizes results from several sources describing quantitative whole fiber analyses of these 22 amino acids. These same amino acids areclassified according to functional group in Table 2.4.
1122 Chemical Composition of Different Hair TypesTable 2.3 Amino acids in whole unaltereda human hair (micromoles per gram dry hair)Amino acidReference Reference Other references1. Aspartic acid444–453b292–578c2. Threonine648–673b588–714705–1,0903. Serine1,013–1091b930–9704. Glutamic acid995–1036b374–694d5. Proline646–708d6. Glycine463–513d548–5603147. Alanine362–384d8. Half-cystine1,407–1,512d1,380–1,500784–1,534 dd9. Valine477–51347047–6710. Methionine50–56b36611. Isoleucine244–255d12. Leucine502–529d489cd13. Tyrosine177–195121–171c14. Phenylalanine132–149d151–226–15. Cysteic acid22–40d16. Lysine206–222b130–212cd17. Histidine64–8640–77511–62018. Arginine499–550d19. Cysteine–41–6617–70 d20. Tryptophan–20–6421. Citrulline––11 % Nitrogen as ammonia15.5–16.9%16.5% aHair is assumed to be cosmetically unaltered for Refs. [14, 15, 17]bNo significant differences among samples analyzedcThe circled values are results of a microbiological assay by Lang and Lucas dSignificant differences indicated among samples analyzedeThese results are a compilation of results from several laboratories and therefore contain no basisfor statistical comparison of each individual amino acid from the different laboratoriesNote the high frequencies of hydrocarbon, hydroxyl, primary amide, and basicamino acid functions in addition to the relatively large disulfide content. The highfrequency of hydrocarbon-containing amino acids confirms that hydrophobicinteractions play a strong role in the reactivity of hair toward cosmetic ingredients.Hydroxyl and amide groups interact through hydrogen bonding interactions, whilethe basic and carboxylic acid groups interact through hydrogen bonding and ionicbonding type interactions.Of particular note is the fact that most of these functional groups occur at higherfrequencies than the disulfide bond in hair. However, these frequencies are wholefiber frequencies, therein assuming that hair is a homogeneous substrate. Thisassumption is certainly not the case, as subsequent sections of this Chapterdemonstrate.Table 2.3 shows substantial variation in the quantities of some of the aminoacids, notably aspartic acid, proline, cystine, and serine, while considerably less
2.2 The Amino Acids and Proteins of Different Types of Hair113Table 2.4 Approximate composition unaltered human hair by amino acid side-chain typeApproximate micromolesAmino acid side-chain typeaper gram hair1. Hydrocarbon (except phenylalanine)2,800Glycine, alanine, valine, leucine, isoleucine, and proline2. Hydroxyl1,750Serine and threonine3. Primary amide carboxylic acid1,450Primary amide (ammonia estimation)1,125Carboxylic acid (by difference)3254. Basic amino acids800Arginine, lysine, and histidine5. Disulfide750Cystine6. Phenolic180TyrosineaSee Table 2.3dispersion is indicated for valine, glutamic acid, glycine, alanine, leucine, andarginine.The following factors can produce differences in whole-fiber amino acid analysis results; genetics, weathering (primarily sunlight exposure), cosmetic treatment,experimental procedures, and diet (not normal diets of healthy individuals, butprotein deficient diets).Marshall and Gillespie  proposed special mathematical relationshipsbetween cystine and leucine:– Leucine (residue %) ¼ 0.31 half-cystine (residue %) 11.3 and betweencystine and proline to determine abnormal variations:– Proline (residue %) ¼ 0.26 half-cystine (residue %) 3.8These relationships are based on the fact that leucine and cystine are commoncomponents of the low sulfur proteins, while proline and cystine are primarycomponents of the high sulfur proteins. They further suggest that the cystinecontent should be about 17–18% and that large variations beyond the calculatedvalues for these three amino acids indicates some cause of variation such as genetic,environmental (sunlight exposure), cosmetic treatment, diet, etc. Variation fromthese factors is described next.126.96.36.199Amino Acid Composition Related to GeneticsThe variation of cystine and cysteine in human hair has been studied extensively.Clay et al.  quantitatively analyzed hair from 120 different persons for cystineand cysteine (see Table 2.3). The hair in this study was selected from both malesand females of varying age and pigmentation. Analysis was by the hydrolytic
1142 Chemical Composition of Different Hair Typesmethod of Shinohara . These results show a wide spread in disulfide contentvarying from 784 to 1,534 mmol half-cystine per gram of hair (8.7–17%); substantially different from the cystine level suggested by Marshall and Gillespie for“normal” hair. Significantly more cystine was found in hair from males thanfemales. Also, dark hair generally contained more cystine than light hair. A similarrelationship between cystine content and hair color has been reported by Oguraet al. .No consistent relationship was found between age and cystine content. Althoughfactors such as diet (malnutrition), cosmetic treatment, and environmental effects(sunlight degradation) may have contributed to variation among these samples,such factors were not considered in this study.With regard to racial variation, nothing has been definitely established. Hawk’sdata  appears to show subtle differences in the relative percentages of variousamino acids found in the hydrolysates of African hair compared to Caucasian hair.Wolfram compiled a more complete set of data from the literature of whole-fiberamino acid analysis of the three major geo-racial groups, showing overlap in theamounts of all the amino acids from scalp hair for these three groups . See thesection in Chap. 1 entitled The Origin of Hair Fiber Curvature which explainsthe distribution and composition of different types of cortical cells in hair. Quantitative protein techniques in the section entitled Major Protein Fractions of Hair inthis Chapter and SNP analysis (Chap. 3) rather than amino acid analysis providesthe best means for determining the differences in the proteins of scalp hair ofdifferent geo-racial groups.188.8.131.52Weathering of Human HairThe photochemical degradation of cystine (see Chap. 5) provides a major cause forvariation in this amino acid among different hair samples. Weathering effects in human hair may be explored by comparing tip ends (longer exposed) to rootends. In a study by Robbins, the cystine and cysteine contents of tip ends wereshown to be lower than in root ends . Complementary to these results, largeramounts of cysteic acid have been reported in hydrolysates of tip ends of humanhair than in root ends . Evidence for cysteic acid in weathered wool has alsobeen provided by Strasheim and Buijs by infrared spectroscopy  and for someSouth African Merino wools by Louw .These results suggest conversion of thioester and cystinyl groups in human hairto higher oxidation states by the elements. This conclusion is supported by the workof Harris and Smith , who determined that ultraviolet light disrupts the disulfidebond of dry wool. In another study, Robbins and Bahl  examined both the effectsof ultraviolet light on hair from root and tip sections from several persons usingelectron spectroscopy for chemical analysis (ESCA) to examine different types ofsulfur in hair. Their data suggested that weathering of cystine in hair is primarily a
2.2 The Amino Acids and Proteins of Different Types of Hair115photochemical reaction proceeding mainly through the C-S fission route producingcystine S-sulfonate residues as a primary end product. This reaction also occurs toa greater extent near the fiber surface showing that oxidation of thioester tosulfonate and loss of MEA also occurs by photochemical degradation. McMillenand Jachowicz  found that Tryptophan is sensitive to degradation by heat. It isalso sensitive to photochemical degradation. Significantly lower quantities of thedibasic amino acids lysine and histidine have been reported in tip ends of humanhair compared to root ends .As indicated, for hair damaged by sunlight, in most cases, the amino acids of thecuticle are altered to a greater extent than those of the cortex because the outerlayers of the fiber receive higher intensities of radiation. Hair protein degradationby light radiation has been shown to occur primarily in the wavelength region of254–400 nm. More recent work by Hoting and Zimmerman  shows that theproteins of the cuticle are degraded by UV-B and UV-A, but less by visible lightand that cystine, proline and valine are degraded more in light brown hair than inblack hair. In other words the photo-protective effect of melanin is much better indark hair than in light hair.Oxidation at the peptide backbone carbon has been shown to occur fromultraviolet exposure both in wool  and in hair [6, 40], producing carbonyl(alpha keto amide intermediates as shown below) which are favored in the drystate reaction more than in the wet state. This reaction is similar to the oxidativedamage to proteins and mitochondrial decay associated with aging described byDean et al.  and described in detail in Chap. 5.R’R-CH-CO-NH-CH-CO-NHuvR-CO-CO-NH- Alpha keto derivative (carbonyl)R’-CH -CO-NHAmideThe photochemical breakdown of disulfide bridges within structural units ofthe A-layer and the exocuticle and matrix of the cortex and the establishment ofnew intra- and intermolecular cross-links via reaction of these carbonyl groups(from uv degradation) with protein amino groups (primarily lysine as shownbelow) within and between structural units decreases structural definition. Thesereactions most likely lead to a gradual increase in brittleness and a gradual loss ofstructural differentiation, see Chap. 5 for details and micrographs that supportthese conclusions.
1162 Chemical Composition of Different Hair TypesR-CO-CO-NHCarbonyl group NH2(CH2)4-CO-CH-NH-R-CH-CO-NHN-H H2O(CH2)4-CO-CH-NHnew cross-linkLysine184.108.40.206Experimental ProceduresThe inconsistent use of correction factors to compensate for hydrolytic decomposition of certain of the amino acids has already been described. In addition, methodsof analysis described in the literature have ranged from wet chemical , tochromatographic , to microbiological . Reexamination of Table 2.3 withthis latter condition in mind shows values for aspartic acid, proline, tyrosine, andlysine as determined by the microbiological assay to be in relatively poor agreement with the other values for these same amino acids determined by wet chemicaland chromatographic procedures. In the case of valine, the values for the microbiological and chromatographic procedures are in close agreement. This suggeststhat for certain of the amino acids (valine) the microbiological assay is satisfactory,whereas for other amino acids (aspartic acid, proline, tyrosine, and lysine), themicrobiological method is questionable.220.127.116.11Stability of Hair KeratinSeveral years ago, a well-preserved cadaver was discovered by archaeologists in theHan Tomb No. 1 near Changsha, China . In the casket, the occupant wore a wellpreserved hair piece that was more than 2,000 years old. Although this hair was notanalyzed for amino acid content, it was analyzed by x-ray diffraction by Kenney, revealing that the alpha-helical content had been well preserved. Nevertheless,some minor disruption of the low ordered matrix had occurred owing to reactionwith a mercurial preservative in the casket. This suggests that the basic structure ofthe intermediate filaments of human hair remains unchanged over centuries and itsessential structural features are extraordinarily stable but the mercury preservativemay be reacting with cystine in the matrix.18.104.22.168Cosmetically Altered HairBleached HairThe whole-fiber amino acid composition of human hair, bleached on the head withcommercial hair-bleaching agents – alkaline hydrogen peroxide or alkaline
2.2 The Amino Acids and Proteins of Different Types of Hair117peroxide/persulfate  has been described in the literature . This investigationdefines the amino acids found in hydrolysates of hair bleached to varying extents onthe head. Data describing frosted (extensively bleached hair using alkaline peroxide/persulfate) vs. non-bleached hair from the same person, bleached on the headabout 1 month prior to sampling, are summarized in Table 2.5. These data show thatthe primary chemical differences between extensively bleached hair and unalteredhair are lower cystine content, a higher cysteic acid content, and lower amounts oftyrosine and methionine in the bleached hair. Mildly to moderately bleached hairshows only significantly lower cystine and correspondingly more cysteic acid thanunaltered hair. These results support Zahn’s  original conclusion that thereaction of bleaching agents with human hair protein occurs primarily at thedisulfide bonds. Fewer total micromoles of amino acids per gram of hair arefound in bleached than in unaltered hair (see Table 2.5) most likely because ofaddition of oxygen to the sulfur containing amino acids and to solubilization ofprotein or protein derived species into the bleach bath .Products of disulfide oxidation, intermediate in oxidation state between cystineand cysteic acid (see Table 2.6), have been shown to be present in wool oxidized byaqueous peracetic acid [46–48]. These same cystine oxides have been demonstratedat low levels in bleached hair ; however, disulfide oxidation intermediates havenot been shown to exist in more than trace amounts in hair oxidized by currentlyused bleaching products .The actual presence of large amounts of cysteic acid in bleached hair had at onetime been in doubt [51, 52]. It had been theorized that the cysteic acid found inTable 2.5 Amino acids from frosted vs. non-frosted hairAmino acidMicromoles per gram hairAspartic acidThreonineSerineGlutamic acidProlineGlycineAlanineHalf enylalanineCysteic acidLysineHistidineArginineNon-frosted 1392719865511Frosted 18055486Significant difference forfrequencies at alpha ¼ 0.01 –––
1182 Chemical Composition of Different Hair TypesTable 2.6 Some possibleoxidation products of thedisulfide ide monoxideDisulfide dioxideDisulfide trioxideDisulfide tetroxideBunte acid or thiosulfonic acidSulfonic acidbleached hair hydrolysates was formed by decomposition of intermediate oxidationproducts of cystine during hydrolysis prior to the analytical procedure . However, differential infrared spectroscopy  and electron spectroscopy for chemicalanalysis by Robbins and Bahl  on intact un-hydrolyzed hair have conclusivelydemonstrated the existence of relatively large quantities of cysteic acid residues inchemically bleached hair. Evidence for other sulfur acids, e.g., sulfinic or sulfenicacids, in bleached hair has not been provided. Furthermore, it is unlikely that theseamino acids exist in high concentrations in hair, because they are relativelyunstable. For details concerning the mechanism of oxidation of sulfur in hair, seeChap. 5.Permanent-Waved HairNineteen amino acids in human hair have been studied for possible modificationduring permanent waving, that is all of the amino acids of Table 2.1 except tryptophan, citrulline and ornithine. Significant decreases in cystine (2–14%) andcorresponding increases in cysteic acid [2, 11] and in cysteine  have been reportedfor human hair that has been treated either on the head by home permanent-wavingproducts or in the laboratory by thioglycolic acid and hydrogen peroxide, in asimulated permanent-waving process.Trace quantities (less than 10 mmol/g) of thioacetylated lysine and sorbedthioglycolic acid have also been reported in human hair treated by cold-wavingreagents . Small quantities of mixed disulfide [2, 6], sorbed dithiodiglycolic acid, and methionine sulfone  have been found in hydrolyzates of hair treated bythe thioglycolate cold-waving d CO2HMethionine sulfoneHOOC-CH2-S-S-CH2-COOHCO2HMixed disulfideDithiodiglycolic acid
2.2 The Amino Acids and Proteins of Different Types of Hair119Methionine sulfone is presumably formed by reaction of the neutralizer withmethionine residues; thioacetylated lyine is probably formed
contributions to the protective properties of the cuticle and the isoelectric point. . C.R. Robbins, Chemical and Physical Behavior of Human Hair, DOI 10.1007/978-3-642-25611-0_2, # Springer-Verlag Berlin Heidelberg 2012 105. damaged by cosmetic chemicals is a new and exciting area for future research. The
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physical education curriculum table of contents acknowledgements 2 district mission statement 3 physical education department mission statement 3 physical education task force 3 physical education and academic performance 4 naspe learning standards 8 new york state physical education learning standards 8 physical education high school curriculum guide 15 physical education curriculum analysis .
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