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BIOCHEMICAL IMPLICATION OF BIOACCUMULATION OF MUSK XYLENE FROM
INDUSTRIAL EFFLUENT
A
SEMINAR
PRESENTED
BY
DAVID, JOSHUA
B.Sc. BIOCHEMISTRY (UPH)
G2016/M.Sc./BCH/FT/023
TO
DEPARTMENT OF BIOCHEMISTRY
FACULTY OF SCIENCE
SCHOOL OF GRADUATE STUDIES
UNIVERSITY OF PORT HARCOURT
COURSE CODE: BCH 818.2
COURSE TITLE: SEMINAR
SUPERVISORS: (1) DR. J. C. IKEWUCHI
(2) DR. D. E. PETERS
SEMINAR CO-ORDINATORS:
DR. (MRS) B. ONYEGEME-OKERENTA
AND
DR. B. A. AMADI
AUGUST, 2017.
INTRODUCTION
Musk compounds are synthetic fragrances.
Classes of synthetic musk fragrances include:
Nitromusks
Polycyclic musks
Macrocyclic musks
and alicyclic (or linear) musks.
Nitromusks were the first produced compounds of this type.
Musk xylene (MX), with the IUPAC nomenclature 1-tert-butyl-5-
dimethyl-2,4,6-trinitrobenzene is a member of this group.
This compound show musk-like odour in spite of the fact that its
structure is very different from natural musk compounds.
It is partially soluble in water (0.15 ng.L-1).
It has relatively high octanol-water partition coefficients (log Kow =
4.9)
MX is also relatively persistent.
According to data published till now:
They are potentially toxic over long time period.
It has been suggested that their transformation products are potentially
highly toxic.
ENVIRONMENTAL CONCERNS
Although human use of household and personal care products containing nitro musks is the
primary route of human exposure, it was the presence of these compounds in environmental
samples that originally drove concern about the biological and environmental effects of nitro
musks in the 1980s.
Studies have shown the presence nitro musk in more than 80% of freshwater fish samples,
river water, and waste water.
MX is not easily degradable, which accounts in part for their widespread presence in
environmental samples.
Nitro musks make their way from personal use settings and into wastewater by:
passage through sewage treatment plants.
By-products of nitro musks have been found in sampled sewage treatment plant effluents.
Furthermore, the biotransformation products of nitro musks created by the sewage treatment
process might also be of interest in risk assessment.
Biotransformation products of MX have been found in aquatic systems at higher
concentrations than the parent compound .
Transformed products of MX are also environmentally persistent.
Wastewater effluent has the ability to affect the concentrations of chemicals in surface water in
the following ways:
When contaminated water sources are used to supply water treatment plants.
Where it used to recharge groundwater.
A vast number of people may be exposed to MX.
TRANSFORMATION PRODUCTS OF MX
Figure 1: UV induced intramolecular reaction of MX
TRANSFORMATION PRODUCTS OF MX Cont.
Figure 2: Bioreduction of MX
ROUTES OF EXPOSURE TO MX
Product Mass fraction (%)
Skin cream 0.0075
Deodorant 0.0075
Shampoo 0.01
Household detergents 0.02
Aftershave 0.03
Toilet soap 0.04
Air freshener 0.07
Cologne 0.075
Fine fragrance 0.05-0.1
Industrial effluent
Personal hygiene products as shown below;
Table 1: Personal hygiene products containing MX
Sources: European Union Risk Assessment Report (2005).
BIOACCUMULATION OF MX AND IMPLICATION
According to the European Union Risk Assessment report (2005) for Musk Xylene:
The report proposed bioaccumulation factor (BCF) of 4,400 l/kg
A number studies reported BCF values between 4,000-5000 l/kg
Calculated BCF based on partition coefficiency of octanol-water (log Kow = 4.9)
is 2900l/kg.
What are the Biochemical Implications of MX?
In particular, the 4-amino-MX transformation product was identified in
the bile, breast milk, faeces as well as in urine.
High serum levels of musk xylene in women has been associated with
gynecological abnormalities, including mild insufficiency of the ovaries
and compromised fertility in women.
Musk xylene may disrupt the human endocrine system.
Animal studies indicate that musk xylene may have carcinogenic
properties.
In particular, liver cancer has been observed in rats treated with musk
xylene
This may be due to the ability of MX to induce specific cytochrome P450
enzymes linked to cancer (e.g CYP2B6 and CYPIA2).
CONCLUSION
The body of literature supports the conclusion that not
only are humans being exposed to MX, but also
bioaccumulating and passing it on to offspring through
breast milk and prenatal exposures. In light of the
foregoing evidence, precautionary principle should be
taken into account. This can be done through a reduction
in the use and production of products containing MX.
REFERENCES
Charles, S. (2005). Ingredients for the Modern Perfumery Industry. The Chemistry of Fragrances (2nd ed.). London:
Royal Society of Chemistry Publishing.
Cornelia S. (2004). The Role of Musk and Musk Compounds in the Fragrance Industry. In Rimkus, G. G. (Ed.),
Synthetic Musk Fragrances in the Environment (Handbook of Environmental Chemistry). UK: Springer.
Daughton, C. and Ternes, T. (2013). Pharmaceuticals and personal care products in the environment: Agents of subtle
change? Environmental Health Perspectives, 107, 907-938.
Eisenhardt, S., Runnebaum, B., Bauer, K. and Gerhard, I. (2001). Nitromusk compounds in women with
gynecological and endocrine dysfunction. Environmental Research Journal, 87(3),123-130.
European Commission Joint Research Centre Institute for Health and Consumer Protection (2005). European Union
Risk Assessment final Report on 5-tert-butyl-2,4,6-trinitro-M-xylene (Musk Xylene) EINECS No: 201-329-4.
The Netherlands.
Haruhiko, N. (2005). Occurrence of Synthetic Musk Fragrances in Marine Mammals and Sharks from Japanese
Coastal Waters Environmental Science and Technology Journal, 39(10), 3430–3434.
Hutter, H. P., Wallner, P., Moshammer, H., Hartl, W., Sattelberger, R., Lorbeer, G. and Kundi, M. (2009). Synthetic
musks in blood of healthy young adults: relationship to cosmetics use. Science and Total Environment Journal,
407(17), 4821-4825.
Iwata, N., Minegishi, K., Suzuki, K., Ohno, Y., Kawanishi, T. and Takahashi, A. (2002). Musk xylene is a novel
specific inducer of cytochrome P-450IA2. Biochemistry and Biophysical Research Communication, 184 (1): 149-
153.
Kathryn, M. T., Marc, W. and James, S. (2014). Human exposure to nitro musks and the evaluation of their potential
toxicity: An overview. Environmental Health Journal, 13, 14-23.
Liebl, B., Mayer, R., Ommer, S., Sonnichsen, C. and Koletzko, B. (2000). Transition of nitro musks and polycyclic
musks into human milk. Advances in Experimental Medicine and Biology, 478, 289–305.
Lignell, S., Darnerud, P. O., Aune, M., Cnattingius, S., Hajslova, J. and Setkova, L. (2008). Temporal trends of
synthetic musk compounds in mother’s milk and associations with personal use of perfumed products.
Environmental Science and Technology Journal, 42(17), 6743–6748.
REFERENCES CONT.
Loretz, L. J., Api, A. M., Barraj, L. M., Burdick, J., Davis D. A., Dressler, W. E. (2006). Exposure data for personal
care products: Hairspray, spray perfume, liquid foundation, shampoo, body wash, and solid antiperspirant. Food
and Chemical Toxicology, 44(12), 2008–2018.
Loretz, L. J., Api, A. M., Barraj, L. M., Burdick, J., Dressler, W. E., Gettings, S. D. (2005). Exposure data for
cosmetic products: lipstick, body lotion, and face cream. Food and Chemical Toxicology, 43(2), 279–291.
Luckenbach, T. and Epel, D. (2005). Nitromusk and polycyclic musk compounds as long-term inhibitors of cellular
xenobiotic defense systems mediated by multidrug transporters. Environmental Health Perspectives, 113(1), 17-
24.
Maekawa, A., Matsushima Y., Onodera, H., Shibutani, M., Ogasawara, H., Kodama, Y., Kurokawa, Y. and Hayashi, Y.
(1990). Long-term toxicity/carcinogenicity of musk xylol in B6C3F1 mice. Food Chemistry Toxicology, 28(8),
581-586.
Peck, A.M. and Hornbuckle, K.C. (2004). Synthetic musk fragrances in Lake Michigan. Environmental Science and
Technology Journal, 38 (2), 367-372.
Reena, K., Sumanth, P. C. and Saraswathi, T. R. (2010). Xylene: An overview of its health hazards and preventive
measures. Journal of Oral and Maxillofacial Pathology, 14(1), 1–5.
Reiner, J. L., Wong, C. M., Arcaro, K.F. and Kannan, K. (2007). Synthetic musk fragrances in human milk from the
United States. Environmental Science Technology Journal, 41(11), 3815-3820.
Salvito, D. (2005). Synthetic musk compounds and effects on human health? Environmental Health Perspectives,
113(12), A802-A803.
Schramm, K., Kaune, A., Beck, B., Thumm, W., Behechti, A. and Kettrup, A. (2006). Acute toxicities of five
nitromusk compounds in Daphnia, algae and photoluminescent bacteria. Water Research Journal, 30(10), 2247-
2250.
Tas, J., Balk, F., Ford, R. and van de Plassche, E. (2007). Environmental risk assessment of musk ketone and musk
xylene in the Netherlands in accordance with the EU-TGD. Chemosphere, 35(12), 2973-3002.
Xiaolan, Z., Gaofeng, L. X., Zeng, J. Z., Guoying, S. and Jiamo F. (2011). Levels of synthetic musk fragrances in
human milk from three cities in the Yangtze River Delta in Eastern China. Journal of Environmental Sciences,
23(6), 983–990.
THANK YOU.

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David, joshua's m.sc. seminar powerpoint presentatation

  • 1. BIOCHEMICAL IMPLICATION OF BIOACCUMULATION OF MUSK XYLENE FROM INDUSTRIAL EFFLUENT A SEMINAR PRESENTED BY DAVID, JOSHUA B.Sc. BIOCHEMISTRY (UPH) G2016/M.Sc./BCH/FT/023 TO DEPARTMENT OF BIOCHEMISTRY FACULTY OF SCIENCE SCHOOL OF GRADUATE STUDIES UNIVERSITY OF PORT HARCOURT COURSE CODE: BCH 818.2 COURSE TITLE: SEMINAR SUPERVISORS: (1) DR. J. C. IKEWUCHI (2) DR. D. E. PETERS SEMINAR CO-ORDINATORS: DR. (MRS) B. ONYEGEME-OKERENTA AND DR. B. A. AMADI AUGUST, 2017.
  • 2. INTRODUCTION Musk compounds are synthetic fragrances. Classes of synthetic musk fragrances include: Nitromusks Polycyclic musks Macrocyclic musks and alicyclic (or linear) musks. Nitromusks were the first produced compounds of this type. Musk xylene (MX), with the IUPAC nomenclature 1-tert-butyl-5- dimethyl-2,4,6-trinitrobenzene is a member of this group. This compound show musk-like odour in spite of the fact that its structure is very different from natural musk compounds. It is partially soluble in water (0.15 ng.L-1). It has relatively high octanol-water partition coefficients (log Kow = 4.9) MX is also relatively persistent. According to data published till now: They are potentially toxic over long time period. It has been suggested that their transformation products are potentially highly toxic.
  • 3. ENVIRONMENTAL CONCERNS Although human use of household and personal care products containing nitro musks is the primary route of human exposure, it was the presence of these compounds in environmental samples that originally drove concern about the biological and environmental effects of nitro musks in the 1980s. Studies have shown the presence nitro musk in more than 80% of freshwater fish samples, river water, and waste water. MX is not easily degradable, which accounts in part for their widespread presence in environmental samples. Nitro musks make their way from personal use settings and into wastewater by: passage through sewage treatment plants. By-products of nitro musks have been found in sampled sewage treatment plant effluents. Furthermore, the biotransformation products of nitro musks created by the sewage treatment process might also be of interest in risk assessment. Biotransformation products of MX have been found in aquatic systems at higher concentrations than the parent compound . Transformed products of MX are also environmentally persistent. Wastewater effluent has the ability to affect the concentrations of chemicals in surface water in the following ways: When contaminated water sources are used to supply water treatment plants. Where it used to recharge groundwater. A vast number of people may be exposed to MX.
  • 4. TRANSFORMATION PRODUCTS OF MX Figure 1: UV induced intramolecular reaction of MX
  • 5. TRANSFORMATION PRODUCTS OF MX Cont. Figure 2: Bioreduction of MX
  • 6. ROUTES OF EXPOSURE TO MX Product Mass fraction (%) Skin cream 0.0075 Deodorant 0.0075 Shampoo 0.01 Household detergents 0.02 Aftershave 0.03 Toilet soap 0.04 Air freshener 0.07 Cologne 0.075 Fine fragrance 0.05-0.1 Industrial effluent Personal hygiene products as shown below; Table 1: Personal hygiene products containing MX Sources: European Union Risk Assessment Report (2005).
  • 7. BIOACCUMULATION OF MX AND IMPLICATION According to the European Union Risk Assessment report (2005) for Musk Xylene: The report proposed bioaccumulation factor (BCF) of 4,400 l/kg A number studies reported BCF values between 4,000-5000 l/kg Calculated BCF based on partition coefficiency of octanol-water (log Kow = 4.9) is 2900l/kg. What are the Biochemical Implications of MX? In particular, the 4-amino-MX transformation product was identified in the bile, breast milk, faeces as well as in urine. High serum levels of musk xylene in women has been associated with gynecological abnormalities, including mild insufficiency of the ovaries and compromised fertility in women. Musk xylene may disrupt the human endocrine system. Animal studies indicate that musk xylene may have carcinogenic properties. In particular, liver cancer has been observed in rats treated with musk xylene This may be due to the ability of MX to induce specific cytochrome P450 enzymes linked to cancer (e.g CYP2B6 and CYPIA2).
  • 8. CONCLUSION The body of literature supports the conclusion that not only are humans being exposed to MX, but also bioaccumulating and passing it on to offspring through breast milk and prenatal exposures. In light of the foregoing evidence, precautionary principle should be taken into account. This can be done through a reduction in the use and production of products containing MX.
  • 9. REFERENCES Charles, S. (2005). Ingredients for the Modern Perfumery Industry. The Chemistry of Fragrances (2nd ed.). London: Royal Society of Chemistry Publishing. Cornelia S. (2004). The Role of Musk and Musk Compounds in the Fragrance Industry. In Rimkus, G. G. (Ed.), Synthetic Musk Fragrances in the Environment (Handbook of Environmental Chemistry). UK: Springer. Daughton, C. and Ternes, T. (2013). Pharmaceuticals and personal care products in the environment: Agents of subtle change? Environmental Health Perspectives, 107, 907-938. Eisenhardt, S., Runnebaum, B., Bauer, K. and Gerhard, I. (2001). Nitromusk compounds in women with gynecological and endocrine dysfunction. Environmental Research Journal, 87(3),123-130. European Commission Joint Research Centre Institute for Health and Consumer Protection (2005). European Union Risk Assessment final Report on 5-tert-butyl-2,4,6-trinitro-M-xylene (Musk Xylene) EINECS No: 201-329-4. The Netherlands. Haruhiko, N. (2005). Occurrence of Synthetic Musk Fragrances in Marine Mammals and Sharks from Japanese Coastal Waters Environmental Science and Technology Journal, 39(10), 3430–3434. Hutter, H. P., Wallner, P., Moshammer, H., Hartl, W., Sattelberger, R., Lorbeer, G. and Kundi, M. (2009). Synthetic musks in blood of healthy young adults: relationship to cosmetics use. Science and Total Environment Journal, 407(17), 4821-4825. Iwata, N., Minegishi, K., Suzuki, K., Ohno, Y., Kawanishi, T. and Takahashi, A. (2002). Musk xylene is a novel specific inducer of cytochrome P-450IA2. Biochemistry and Biophysical Research Communication, 184 (1): 149- 153. Kathryn, M. T., Marc, W. and James, S. (2014). Human exposure to nitro musks and the evaluation of their potential toxicity: An overview. Environmental Health Journal, 13, 14-23. Liebl, B., Mayer, R., Ommer, S., Sonnichsen, C. and Koletzko, B. (2000). Transition of nitro musks and polycyclic musks into human milk. Advances in Experimental Medicine and Biology, 478, 289–305. Lignell, S., Darnerud, P. O., Aune, M., Cnattingius, S., Hajslova, J. and Setkova, L. (2008). Temporal trends of synthetic musk compounds in mother’s milk and associations with personal use of perfumed products. Environmental Science and Technology Journal, 42(17), 6743–6748.
  • 10. REFERENCES CONT. Loretz, L. J., Api, A. M., Barraj, L. M., Burdick, J., Davis D. A., Dressler, W. E. (2006). Exposure data for personal care products: Hairspray, spray perfume, liquid foundation, shampoo, body wash, and solid antiperspirant. Food and Chemical Toxicology, 44(12), 2008–2018. Loretz, L. J., Api, A. M., Barraj, L. M., Burdick, J., Dressler, W. E., Gettings, S. D. (2005). Exposure data for cosmetic products: lipstick, body lotion, and face cream. Food and Chemical Toxicology, 43(2), 279–291. Luckenbach, T. and Epel, D. (2005). Nitromusk and polycyclic musk compounds as long-term inhibitors of cellular xenobiotic defense systems mediated by multidrug transporters. Environmental Health Perspectives, 113(1), 17- 24. Maekawa, A., Matsushima Y., Onodera, H., Shibutani, M., Ogasawara, H., Kodama, Y., Kurokawa, Y. and Hayashi, Y. (1990). Long-term toxicity/carcinogenicity of musk xylol in B6C3F1 mice. Food Chemistry Toxicology, 28(8), 581-586. Peck, A.M. and Hornbuckle, K.C. (2004). Synthetic musk fragrances in Lake Michigan. Environmental Science and Technology Journal, 38 (2), 367-372. Reena, K., Sumanth, P. C. and Saraswathi, T. R. (2010). Xylene: An overview of its health hazards and preventive measures. Journal of Oral and Maxillofacial Pathology, 14(1), 1–5. Reiner, J. L., Wong, C. M., Arcaro, K.F. and Kannan, K. (2007). Synthetic musk fragrances in human milk from the United States. Environmental Science Technology Journal, 41(11), 3815-3820. Salvito, D. (2005). Synthetic musk compounds and effects on human health? Environmental Health Perspectives, 113(12), A802-A803. Schramm, K., Kaune, A., Beck, B., Thumm, W., Behechti, A. and Kettrup, A. (2006). Acute toxicities of five nitromusk compounds in Daphnia, algae and photoluminescent bacteria. Water Research Journal, 30(10), 2247- 2250. Tas, J., Balk, F., Ford, R. and van de Plassche, E. (2007). Environmental risk assessment of musk ketone and musk xylene in the Netherlands in accordance with the EU-TGD. Chemosphere, 35(12), 2973-3002. Xiaolan, Z., Gaofeng, L. X., Zeng, J. Z., Guoying, S. and Jiamo F. (2011). Levels of synthetic musk fragrances in human milk from three cities in the Yangtze River Delta in Eastern China. Journal of Environmental Sciences, 23(6), 983–990.