PMID- 24962464
OWN - NLM
STAT- MEDLINE
DCOM- 20150514
LR  - 20140911
IS  - 1468-2494 (Electronic)
IS  - 0142-5463 (Linking)
VI  - 36
IP  - 5
DP  - 2014 Oct
TI  - Formaldehyde replacement with glyoxylic acid in semipermanent hair straightening: 
      a new and multidisciplinary investigation.
PG  - 459-70
LID - 10.1111/ics.12148 [doi]
AB  - OBJECTIVE: Formaldehyde is an effective and popular semipermanent hair 
      straightener, but the severe consequences for human health due to its toxicity 
      have prompted the search for safer alternatives. Different carbonyl compounds, 
      including glyoxylic acid, have recently been proposed as promising candidates. 
      Despite the interest in this topic, there is a lack of information about the 
      interactions between hair keratin and straightener agents. This study addresses 
      this issue to gain new insights useful in the development of new products for 
      safe, semipermanent hair deformation. METHODS: The possible reactions occurring 
      between carbonyl groups and nucleophilic sites on amino acid residues belonging 
      to the keratin were investigated using as model compounds some aldehydes and 
      amino acid derivatives. Raman and IR analyses on yak hair subjected to the 
      straightening treatment with glyoxylic acid in different conditions were carried 
      out. Scanning electron microscope (SEM) analyses were carried out on yak and 
      curly human hair after each step of the straightening procedure. RESULTS: The 
      reactions between aldehydes and N-alpha-acetyl-L-lysine revealed the importance of 
      the carbonyl electrophilicity and temperature to form imines. Raman and IR 
      analyses on yak hair subjected to the straightening treatment evidenced 
      rearrangements in the secondary structure distribution, conformational changes to 
      the disulphide bridges, a decrease of the serine residues and formation of 
      imines. It was also indicated that straightening produced major conformational 
      rearrangements within the hair fibre rather than on the cuticle. CONCLUSION: This 
      investigation revealed the role played by the electrophilicity of the carbonyl on 
      the straightener agent and of the temperature, closely related to the dehydration 
      process. Raman and IR studies indicated the involvement of imine bonds and the 
      occurrence of a sequence of conformational modifications during the straightening 
      procedure. SEM analyses showed the effectiveness of the treatment at the 
      cuticular level.
CI  - (c) 2014 Society of Cosmetic Scientists and the Societe Francaise de Cosmetologie.
FAU - Boga, C
AU  - Boga C
AD  - Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum- 
      University of Bologna, Viale del Risorgimento 4, 40136, Bologna, Italy.
FAU - Taddei, P
AU  - Taddei P
FAU - Micheletti, G
AU  - Micheletti G
FAU - Ascari, F
AU  - Ascari F
FAU - Ballarin, B
AU  - Ballarin B
FAU - Morigi, M
AU  - Morigi M
FAU - Galli, S
AU  - Galli S
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20140811
PL  - England
TA  - Int J Cosmet Sci
JT  - International journal of cosmetic science
JID - 8007161
RN  - 0 (Aldehydes)
RN  - 0 (Amino Acids)
RN  - 0 (Glyoxylates)
RN  - 0 (Hair Preparations)
RN  - 1HG84L3525 (Formaldehyde)
RN  - JQ39C92HH6 (glyoxylic acid)
SB  - IM
MH  - Aldehydes/chemistry
MH  - Amino Acids/chemistry
MH  - *Formaldehyde
MH  - *Glyoxylates
MH  - *Hair Preparations
MH  - Humans
MH  - Microscopy, Electron, Scanning
MH  - Models, Chemical
MH  - Spectroscopy, Fourier Transform Infrared
MH  - Spectrum Analysis, Raman
OTO - NOTNLM
OT  - chemical synthesis
OT  - glyoxylic acid
OT  - hair treatment
OT  - keratin
OT  - spectroscopy
OT  - straightening
EDAT- 2014/06/26 06:00
MHDA- 2015/05/15 06:00
CRDT- 2014/06/26 06:00
PHST- 2014/04/11 00:00 [received]
PHST- 2014/06/08 00:00 [accepted]
PHST- 2014/06/26 06:00 [entrez]
PHST- 2014/06/26 06:00 [pubmed]
PHST- 2015/05/15 06:00 [medline]
AID - 10.1111/ics.12148 [doi]
PST - ppublish
SO  - Int J Cosmet Sci. 2014 Oct;36(5):459-70. doi: 10.1111/ics.12148. Epub 2014 Aug 
      11.