Page 222 Surface analysis of permanent wave processing hair using DART-MS
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1 Life Science
2 Page 222 Surface analysis of permanent wave processing hair using DART-MS Page 229 Analysis of allergens found in cosmetics using MDGC-GCMS (Multi-Dimensional Gas Chromatograph Mass Spectrometer)
3 PO-CON1454E Surface analysis of permanent wave processing hair using DART-MS ASMS 2014 MP 476 Shoji Takigami 1, Erika Ikeda 1, Yuta Takagi 1, Jun Watanabe 2, Teruhisa Shiota 3 1 Gunma University, Kiryu, Japan; 2 Shimadzu Corporation, Nakagyo-ku, Kyoto, Japan; 3 AMR Inc., Meguro-ku, Tokyo, Japan
4 Surface analysis of permanent wave processing hair using DART-MS Introduction Permanent wave processing of hair is carried out at two processes as follows; (A) Reducing agent (permanent wave 1 agent) makes the bridge construction between the keratin protein molecular chains of hair, especially disulfide (S-S) bond of cystine residue cleaved to thiol (-SH) group and hear results a wave and curl. (B) Oxidizing agent (permanent wave 2 agent) makes -SH group oxidized to be reproduced S-S bond. As reducing agents used for permanent wave 1 agent, the thing of cosmetics approval, such as cysteamine hydrochloride and a butyrolactone thiol (brand name Spiera, other than quasi drugs, such as ammonium thioglycolate, acetyl cystein, and thiolactic acid, are used. After hair is applying permanent wave processing and coloring repeatedly, the chemical structure of a keratin molecule and fine structure in the hair have been damaged and it resulted as damage hair. It is thought that hair becomes dryness and twining if the cuticle which covers hair is damaged, so it is important to investigate the surface structure of hair and its chemical structure changing. DART (Direct Analysis in Real Time), a direct atmospheric pressure ionization source, is capable of analyzing samples directly with little or no sample preparation. Here, analysis of the ingredient which has deposited on the permanent wave processing hair surface was tried using this DART combined with a mass spectrometer. High Speed Mass Spectrometer Ufswitching High-Speed Polarity Switching 15msec Ufscanning High-Speed Scanning 15,000u/sec Figure 1 DART-OS ion source & LCMS-2020 TGA (thioglycolate) HO O SH CA (cysteamine hydrochloride) HCl H 2 N SH BLT (butyrolactone thiol) O O SH Fw 92 Fw 113 Fw 118 Wave efficiency is good in a weak alkaline (ph 8-9.5) Wave efficiency is good in a weak alkaline (ph 8-9.5) Wave efficiency is good in a weak acid (ph 6) The chemical state and property were investigated in the surface of the hair which repeated permanent wave processing with these reducing agents. 2
5 Surface analysis of permanent wave processing hair using DART-MS Methods and Materials The Chinese virgin hair purchased from the market was washed with the 0.5% non-ionic surfactant containing saturated EDTA solution, and then it was considered as untreated hair sample. Permanent wave processing of hair was prepared as following; the 0.6M TGA solution and 0.6M CA solution which were adjusted to ph8.5 with aqueous ammonia and the 0.6M BLT solution adjusted to ph6.0 with arginine water, which were used as a reducing agent. After hair sample was reduced for 15 minutes at 35 C using each solvent, it was carried out oxidation treatment at 35 C by being immersed in 8% sodium bromate solution (ph7.2) for 15 minutes. LCMS-2020 (Shimadzu) was coupled with DART-OS ion source (IonSense) and hear samples were held onto DART gas flow directly, then their surface analyzed. MS condition (LCMS-2020; Shimadzu Corporation) Ionization : DART (Direct Analysis in Real Time) Heater Temperature (DART) : 350 C Measuring mode (MS) : Positive/Negative scanning simultaneously Chinese Virgin Hair 0.5% Laureth - 9 solution - EDTA saturated 35 C 1h Water washing and air drying Untreated Repeat 6 times Permanent wave processing by agent 1 & 2 at 0.6M each permanent wave 1 agent : TGA or CA (ph 8.5; aqueous ammonium) BLT (ph 6; arginine) 35 C 15min Water washing permanent wave 2 agent : 8% NaBrO3 solution (ph 7.2) 35 C 15min Water washing Britton - Robinson buffer (ph 4.6) 35 C 15min Water washing Air drying Analyzed by DART-MS 3
6 Surface analysis of permanent wave processing hair using DART-MS Result After repeating operation of permanent wave processing 1-6 times using TGA (thioglycollic acid), CA (cysteamine), and BLT (Butyrolactonethiol), hair was immersed for 15 minutes at 35 C and with a flush and air-drying, then permanent wave processing hair was prepared. In order to investigate the ingredient which has deposited on the permanent wave processing hair surface, DART-MS analysis was performed. DART-MS analysis was conducted in order of #1 Untreated (woman hair), #2 control; ammonia treatment (ph 8.5), #3 0.6M thioglycolic acid (TGA) processing, #4 0.6M butyrolactone thiol (BLT) processing, #5 0.6M cysteamine hydrochloride (CA) processing and #6 control; arginine processing (ph 6) :TIC(+) #1 #2 #3 #4 #5 #6 Positive TIC m/z :TIC(-) Negative TIC m/z min Figure 2 TIC chromatogram of each sample analyzing with DART In the DART mass spectra of #1 untreated and #6 control, many signals considered as triglyceride and diglyceride were detected in both positive and negative spectra obtained by DART-MS. In #3 0.6M thioglycolic acid (TGA) processing spectra, the signal in particular of TGA origin was not detected. In #4 BLT processing spectra (Figure 3), the signals considered to be oxidized BLT (3, 3'-dithiobis (tetrahydrofuran2-one), molecular weight 234) were detected at m/z 235 and 252 in the positive mode. The signal m/z 235 is equivalent to [M+H]+ and m/z 252, [M+NH4]+. In the negative mode, the signals, m/z 115, 231 were detected. They were considered the signal equivalent to [M-H]- and [2M-H]- of BLT oxide compound (C4H4O2S, molecular weight 116) in which two hydrogen atoms were removed from BLT. Carrying out permanent wave processing by BLT, it was found that the dimer of BLT accumulated on the cuticle surface. In #5 CA processing spectrum (Figure 5), the signal considered to be the dimer (Fw152) origin in which CA carried out S-S bond in the positive mode was detected at m/z 153. This is equivalent to [M+H]+. 4
7 Surface analysis of permanent wave processing hair using DART-MS Inten (x10,000,000) 252 [M+NH4]+ [M+H]+ 235 Positive m/z Inten. (x100,000) [M-H]- 115 [2M-H]- 231 Negative m/z Figure 3 DART-MS spectra of #4 BLT processing The BLT-related signals were detected from the positive and the negative spectra. Inten. (x1,000,000) Positive [2M+H] m/z Figure 4 DART-MS spectra of #5 CA processing The CA-related signal was detected from the positive spectrum 5
8 Surface analysis of permanent wave processing hair using DART-MS :325.15(-) #1 #2 #3 #4 #5 #6 Negative XIC m/z :234.70(+) Positive XIC m/z :251.75(+) Positive XIC m/z :114.95(-) Negative XIC m/z :230.90(-) Negative XIC m/z :123.85(+) Positive XIC m/z :152.85(+) Positive XIC m/z min Figure 5 XIC chromatorgam of each sample analyzing with DART In order to indicate clearly the signals specifically detected in each sample, the extraction chromatograms (XIC) were shown (Figure 5). It turned out that BLT-related signals were detected only in #4 and the CA-related signal in #5. Moreover, although the signal intensity was weak, the signal at negative m/z 325 was detected from all samples. Negative m/z 325 is equivalent to [M-H]- of 18 methyl eicosanoic acid (18MEA, molecular weight 326). 18MEA is one of lipid components which protect a cuticle. There is no significant difference of this signal in the hair between treated hair and untreated hair. We would like to inquire so that intensity difference can be found out by further verifying the detection technique in the future. 6
9 Surface analysis of permanent wave processing hair using DART-MS Conclusions By direct analysis of the hair by DART-MS, the chemical structure change in the surfaces of hair, such as permanent wave processing, was able to be observed. First Edition: June, For Research Use Only. Not for use in diagnostic procedures. The content of this publication shall not be reproduced, altered or sold for any commercial purpose without the written approval of Shimadzu. The information contained herein is provided to you "as is" without warranty of any kind including without limitation warranties as to its accuracy or completeness. Shimadzu does not assume any responsibility or liability for any damage, whether direct or indirect, relating to the use of this publication. This publication is based upon the information available to Shimadzu on or before the date of publication, and subject to change without notice. Shimadzu Corporation, 2014
10 PO-CON1469E Analysis of allergens found in cosmetics using MDGC-GCMS (Multi-Dimensional Gas Chromatograph Mass Spectrometer) ASMS 2014 TP761 Sanket Chiplunkar, Prashant Hase, Dheeraj Handique, Ankush Bhone, Durvesh Sawant, Ajit Datar, Jitendra Kelkar, Pratap Rasam Shimadzu Analytical (India) Pvt. Ltd., 1 A/B Rushabh Chambers, Makwana Road, Marol, Andheri (E), Mumbai , Maharashtra, India.
11 Analysis of allergens found in cosmetics using MDGC-GCMS (Multi-Dimensional Gas Chromatograph Mass Spectrometer) Introduction Cosmetics, fragrances and toiletries (Figure 1) are used safely by millions of people worldwide. Although many people have no problems, irritant and allergic reactions may occur. Irritant and allergic skin reactions are the types of contact dermatitis. Essential oils present in fragrance contain some natural and synthetic compounds, which may cause allergic reactions to the end user after application. There are 26 potential allergens listed by European Directive (EU) 2003/15/EC and International Fragrance Association (IFRA) [1] labeled on cosmetics. Shimadzu MDGC-GCMS technology facilitates the identification and quantification of these allergens to comply with the threshold limits of 100 ppm for rinse-off products. Co-eluting peaks were resolved completely with the help of MDGC-GCMS heart-cut technique. Figure 1. Cosmetics, fragrances and toiletries Method of Analysis Extraction of allergens from shampoo sample Shampoo samples were collected from local market. Standard solutions of 23 allergens were procured from ACCU Standard and dilutions were carried out in Ethanol/Acetonitrile to yield 1000 ppm concentration. Further dilutions were made in methanol. MDGC-GCMS technique was effectively used to minimize matrix effect. Co-eluting peaks were resolved with heart-cut technique using two columns of different polarities. In MDGC-GCMS, 1 st instrument was GC-2010 Plus equipped with FID as a detector and 2 nd instrument was GCMS-QP2010 Ultra with MS as a detector. Columns in both the instruments were connected with Deans switch. Allergens in shampoo samples were determined by using this technique. For sample preparation, following methodology was adopted. 1) Blank Solution : 10 ml of methanol was transferred in 20 ml centrifuge tube and vortexed for 5 minutes. The mixture was then centrifuged for 5 minutes at 3000 rpm. This solution was filtered through 0.2 µm nylon syringe filter. Initial 2 ml was discarded and remaining filtrate was collected. 2) Sample Solution : 1 g of shampoo sample was weighed in 10 ml volumetric flask and diluted up to the mark with methanol. Above mixture was transferred in 20 ml centrifuge tube. Further processing was done as mentioned in blank solution. 3) Spike Sample Solution : For recovery study, 1 g of sample was spiked with different volumes of standard stock solution. The above procedure was repeated for preparing different concentration levels of allergens in samples. These spiked samples were treated as mentioned in sample solution. Part method validation was carried out by performing system precision, sample precision, linearity and recovery study. For validation, solutions of different concentrations were prepared using 40 ppm (actual concentration) standard stock solution mixture of allergens. 2
12 Analysis of allergens found in cosmetics using MDGC-GCMS (Multi-Dimensional Gas Chromatograph Mass Spectrometer) Table 1. Method validation parameters Parameter System Precision Sample Precision Linearity Accuracy / Recovery Concentration 10 ppm 10 % in Methanol 2.5, 5, 7.5, 10, 15 (ppm) 5, 10, 15 (ppm) MDGC-GCMS Analytical Conditions The instrument configuration used is shown in Figure 2. Samples were analyzed using Multi-Dimensional GC/GCMS as per the conditions given below. Figure 2. Multi-Dimensional GC/GCMS System by Shimadzu Figure 3. Schematic diagram of multi-deans switch in MDGC-GCMS 3
13 Analysis of allergens found in cosmetics using MDGC-GCMS (Multi-Dimensional Gas Chromatograph Mass Spectrometer) MDGC-GCMS analytical parameters Chromatographic parameters (1 st GC : GC-2010 Plus) Column : Stabilwax (30 m L x 0.25 mm I.D.; 0.25 μm) Injection Mode : Split Split Ratio : 5.0 Carrier Gas : Helium Column Flow : 2.27 ml/min Detector : FID APC Pressure : 200 kpa (For switching) Column Oven Temp. : Rate (ºC /min) Temperature (ºC) Hold time (min) Chromatographic parameters (2 nd GCMS : GCMS-QP2010 Ultra) Column : Rxi-1ms (30 m L x 0.25 mm I.D.; 0.25 μm) Detector : Mass spectrometer Ion Source Temp. : 200 ºC Interface Temp. : 240 ºC Ionization Mode : EI Event Time : 0.30 sec Mode : SIM and SCAN Column Oven Temp. : Rate (ºC /min) Temperature (ºC) Hold time (min) Total Program Time : min Results Sample analysis using MDGC-GCMS MDGC-GCMS technique was used to avoid matrix interference from sample. Using multi-deans switch and heart-cut technique (Figure 3), co-eluted components from the 1 st column were transferred to the 2 nd column with different polarity. 4
14 Analysis of allergens found in cosmetics using MDGC-GCMS (Multi-Dimensional Gas Chromatograph Mass Spectrometer) uv (x100,000) Chromatogram Sample - 1 Limonene Linalool Methyl heptine carbonate Sample - 2 Sample - Citral uv (x10,000) Chromatogram min Citral - 2 Citronellol Methyl heptine carbonate Sample - 2 Sample - 3 Citral - 1 Geraniol Benzyl Alcohol Citral - 2 Hydroxy-citronellal Citronellol Cinnamal Geraniol Benzyl Alcohol Eugenol Amyl cinnamal Cinnamyl alcohol Anisyl alcohol Fernesol - 1 Fernesol - Isoeugenol 2 Fernesol - 2 Hexyl cinnam aldehyde uv (x10,000) Chromatogram Coumarin Amylcin namyl alcohol Amyl cinnamal Anisyl alcohol Cinnamyl alcohol min Sample - 5 Benzyl benzoate Fernesol - 1 Isoeugenol Sample - 6 Fernesol - 2 Fernesol - 2 Hexyl cinnam aldehyde Benzyl salicylate Benzyl Cinnamate min Figure 4. Chromatogram of spiked sample solution before switching uv (x10,000) Chromatogram Target compound - Isoeugenol min Figure 5. Chromatogram with 1 st column (FID) (x100,000) (100.00) (100.00) (100.00) (100.00) (100.00) (100.00) (100.00) (100.00) (100.00) Target compound - Isoeugenol Figure 6. SIM chromatogram with 2 nd column (MS) Summary of results Table 2. Summary of results for precision on GC and GCMS Sr. No. Type of sample Sample name Concentration Result 1 Standard 23 Allergens mixture 10 ppm % RSD for area (n=6) < Cosmetic Shampoo Unknown % RSD for area (n=6) < 2.0 5
15 Analysis of allergens found in cosmetics using MDGC-GCMS (Multi-Dimensional Gas Chromatograph Mass Spectrometer) Sr. No. 1 2 Table 3. Linearity by GC Name of allergen Linalool Methyl heptine carbonate Linearity (R 2 ) Area (x10,000) 3 Citronellol Geraniol Hydroxy citronellal Cinnamal Amyl Cinnamal Coumarin Amylcin namyl alcohol Benzyl benzoate Conc. Figure 7. Linearity graph for linalool Sr. No. 1 Table 4. Linearity by GCMS Name of allergen Limonene Linearity (R 2 ) Area(x10,000) 2 Benzyl alcohol Citral - 1 Citral Eugenol Anisyl alcohol Cinnamyl alcohol Isoeugenol Farnesol - 1 Farnesol Hexyl cinnam aldehyde Benzyl salicylate Benzyl cinnamate Conc. Figure 8. Linearity graph for benzyl cinnamate Quantitation of allergens in shampoo sample For the quantitation studies, the shampoo sample was spiked with allergens standard to achieve 5, 10 and 15 ppm concentrations. Recovery studies were performed on 13 allergens, having co-elution or matrix interference, using heart-cut technique. The quantitation of these allergens was carried out using 2 nd detector (MS) in SIM mode. In below recovery study, some allergens had recovery value out side the acceptance limit ( %). Optimization can be done by means of change in sample clean up procedure and filtration study. 6
16 Analysis of allergens found in cosmetics using MDGC-GCMS (Multi-Dimensional Gas Chromatograph Mass Spectrometer) Sr. No Table 5. Quantitation of allergens Recovery Study Name of allergen Limonene Benzyl alcohol Citral - 1 Citral - 2 Eugenol Anisyl alcohol Cinnamyl alcohol Isoeugenol Farnesol - 1 Farnesol - 2 Hexyl cinnam aldehyde Benzyl salicylate Benzyl cinnamate Level -1 5 ppm % Recovery Level ppm Level ppm (x1,000) m/z : Farnesol-1 Farnesol-2 Spiked Unspiked Figure 9. Overlay SIM chromatogram of unspiked and spiked sample min Conclusion MDGC-GCMS method was developed for quantitation of allergens present in cosmetics. Part method validation was performed as per ICH guidelines. [2] Results obtained for reproducibility, linearity and recovery studies were well within acceptable limits. Simultaneous SCAN/SIM and high-speed scan rate 20,000 u/sec are the characteristic features of GCMS-QP2010 Ultra, which enables quantitation of allergens at very low concentration level. Matrix effect from cosmetics was selectively eliminated using MDGC-GCMS with multi-deans switching unit and heart-cut technique. MDGC-GCMS was found to be very useful technique for simultaneous identification and quantitation of components from complex matrix. Reference [1] IFRA guidelines (International Fragrance Association), GC/MS Quantification of potential fragrance allergens, Version 2, (2006), 6. [2] ICH guidelines, Validation of Analytical Procedures: Text And Methodology Q2(R1), Version 4, (2005). First Edition: June, For Research Use Only. Not for use in diagnostic procedures. The content of this publication shall not be reproduced, altered or sold for any commercial purpose without the written approval of Shimadzu. The information contained herein is provided to you "as is" without warranty of any kind including without limitation warranties as to its accuracy or completeness. Shimadzu does not assume any responsibility or liability for any damage, whether direct or indirect, relating to the use of this publication. This publication is based upon the information available to Shimadzu on or before the date of publication, and subject to change without notice. Shimadzu Corporation, 2014
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