Timol: Perbedaan antara revisi
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'''Timol''' (juga dikenal sebagai '''2-isopropil-5-metilfenol''', disingkat '''IPMP''') adalah turunan [[fenol]] [[Monoterpena|monoterpenoid]] alami dari ''p''-
==Sejarah==
Orang [[Mesir Kuno]] menggunakan timi untuk [[pembalsaman]].<ref>{{Cite web|url=http://www.history.com/news/hungry-history/a-brief-history-of-thyme|title=A Brief History of Thyme - Hungry History|website=HISTORY.com|access-date=2016-06-09|url-status=live|archive-url=https://web.archive.org/web/20160613081647/http://www.history.com/news/hungry-history/a-brief-history-of-thyme|archive-date=2016-06-13}}</ref> Orang-orang [[Yunani Kuno]] menggunakannya di pemandian mereka dan membakarnya sebagai [[dupa]] di [[kuil]]-kuil mereka karena diyakini sebagai sumber [[keberanian]]. Penyebaran timi ke seluruh Eropa dianggap disebarkan oleh bangsa [[Romawi Kuno]], karena mereka menggunakannya untuk memurnikan kamar mereka dan untuk "memberikan rasa aromatik pada keju dan [[likeur]]".<ref name=Maud>{{cite web|url=http://botanical.com/botanical/mgmh/t/thygar16.html|title=Thyme. A Modern Herbal|edition=Hypertext version of the 1931|work=botanical.com|last=Grieve|first=Mrs. Maud|access-date=9 February 2008|url-status=live|archive-url=http://archive.wikiwix.com/cache/20110223130247/http://botanical.com/botanical/mgmh/t/thygar16.html|archive-date=23 February 2011}}</ref> Pada [[Abad Pertengahan]] Eropa, ramuan ini ditempatkan di bawah bantal untuk membantu tidur dan mengusir mimpi buruk.<ref name=Huxley>Huxley, A., ed. (1992). ''New RHS Dictionary of Gardening''. Macmillan.</ref> Pada masa ini, para wanita juga sering memberikan hadiah kepada ksatria dan pejuang, diantaranya daun timi, karena diyakini dapat memberikan keberanian bagi pemakainya. Timi juga digunakan sebagai dupa dan ditempatkan di peti mati selama upacara pemakaman, karena dianggap menjamin perjalanan menuju kehidupan selanjutnya.<ref>{{cite web|url=http://www.englishplants.co.uk/thyme.html|title=Thyme (thymus)|work=englishplants.co.uk|publisher=The English Cottage Garden Nursery|url-status=live|archive-url=https://web.archive.org/web/20060927050614/http://www.englishplants.co.uk/thyme.html|archive-date=2006-09-27}}</ref>
Tumbuhan balm lebah ''Monarda fistulosa'' dan ''Monarda didyma'', spesies bunga liar Amerika Utara, merupakan sumber timol alami. Penduduk asli Amerika [[Konfederasi Blackfoot]] mengenali tindakan antiseptik yang kuat dari tanaman ini dan menggunakan [[tuam (medis)|tuam]] dari tanaman tersebut untuk infeksi kulit dan luka ringan. [[Teh herbal]] yang dibuat darinya juga digunakan untuk mengobati infeksi mulut dan tenggorokan yang disebabkan oleh [[karies gigi]] dan [[gingivitis]].<ref>{{cite book|last=Tilford |first=Gregory L. |date=1997 |title=Edible and Medicinal Plants of the West |location=Missoula, MT |publisher=Mountain Press Publishing |isbn=978-0-87842-359-0}}</ref>
Timol pertama kali diisolasi oleh kimiawan Jerman Caspar Neumann pada tahun 1719.<ref>{{cite journal|first=Carolo |last=Neuman |date=1724 |title=De Camphora |journal=Philosophical Transactions of the Royal Society of London |volume=33 |issue=389 |pages=321–332 |url=http://rstl.royalsocietypublishing.org/content/33/381-391/321.full.pdf+html |doi=10.1098/rstl.1724.0061|doi-access=free }} On page 324, Neumann mentions that in 1719 he distilled some essential oils from various herbs. On page 326, he mentions that during these experiments, he obtained a crystalline substance from thyme oil, which he called "''Camphora Thymi''" ([[camphor]] of thyme). (Neumann gave the name "camphor" not only to the specific substance that today is called camphor but to any crystalline substance that precipitated from a volatile, fragrant oil from some plant.)</ref> Pada tahun 1853, ahli kimia Perancis Alexandre Lallemand (1816-1886)<ref>Marie-Étienne-Alexandre Lallemand (December 25, 1816 - March 16, 1886)</ref> menamai timol dan menentukan rumus empirisnya.<ref>{{cite journal|first=A. |last=Lallemand |date=1853 |url=http://gallica.bnf.fr/ark:/12148/bpt6k29948/f502.image.langEN |title=Sur la composition de l'huile essentielle de thym |trans-title=On the composition of the essential oil of thyme |language=fr |journal=Comptes Rendus |volume=37 |pages=498–500}}</ref> Timol pertama kali disintesis oleh ahli kimia Swedia Oskar Widman<ref>Karl Oskar Widman (aka Carl Oskar Widman) (January 2, 1852 - August 26, 1930)</ref> (1852-1930) pada tahun 1882.<ref>{{cite journal|first=Oskar |last=Widmann |date=1882 |url=http://gallica.bnf.fr/ark:/12148/bpt6k90694n/f169.image.langEN |title=Ueber eine Synthese von Thymol aus Cuminol |trans-title=On a synthesis of thymol from cuminol |language=de |journal=Berichte der Deutschen Chemischen Gesellschaft zu Berlin |volume=15 |pages=166–172 |doi=10.1002/cber.18820150139}}</ref>
==Sintesis kimia==
Timol diproduksi melalui [[alkilasi]] ''m''-kresol dan [[propena]]:<ref>{{cite book|last1=Stroh|first1=R.|last2=Sydel|first2=R.|last3=Hahn|first3=W.|editor1-last=Foerst|editor1-first=Wilhelm|title=Newer Methods of Preparative Organic Chemistry, Volume 2|date=1963|publisher=Academic Press|location=New York|isbn=9780323150422|page=344|edition= 1st|url=https://books.google.com/books?id=LG2J6i1sUAMC&pg=PA344}}</ref><ref>{{Ullmann |doi=10.1002/14356007.a19_313|title=Phenol Derivatives |year=2000 |last1=Fiege |first1=Helmut |last2=Voges |first2=Heinz-Werner |last3=Hamamoto |first3=Toshikazu |last4=Umemura |first4=Sumio |last5=Iwata |first5=Tadao |last6=Miki |first6=Hisaya |last7=Fujita |first7=Yasuhiro |last8=Buysch |first8=Hans-Josef |last9=Garbe |first9=Dorothea |last10=Paulus |first10=Wilfried |isbn=3527306730 }}</ref>
: {{chem2|CH3C6H4OH + CH2CHCH3 -> ((CH3)2CH)CH3C6H3OH}}
Metode biosintesis timol yang diprediksi dalam timi dan oregano dimulai dengan siklisasi geranil difosfat oleh TvTPS2 menjadi γ-terpinena. Oksidasi oleh [[sitokrom P450]] di subfamili CYP71D menghasilkan zat antara dienol, yang kemudian diubah menjadi keton oleh dehidrogenase rantai pendek. Terakhir, tautomerisasi keto-enol menghasilkan timol.
[[File:Thymol biosynthesis.svg|center|thumb|800px|Prediksi biosintesis timol pada timi dan oregano. Rekonstruksi gambar 4 di Krause ''et. al.'' (2021).<ref name="r505">{{cite journal | last=Krause | first=Sandra T. | last2=Liao | first2=Pan | last3=Crocoll | first3=Christoph | last4=Boachon | first4=Benoît | last5=Förster | first5=Christiane | last6=Leidecker | first6=Franziska | last7=Wiese | first7=Natalie | last8=Zhao | first8=Dongyan | last9=Wood | first9=Joshua C. | last10=Buell | first10=C. Robin | last11=Gershenzon | first11=Jonathan | last12=Dudareva | first12=Natalia | last13=Degenhardt | first13=Jörg | title=The biosynthesis of thymol, carvacrol, and thymohydroquinone in Lamiaceae proceeds via cytochrome P450s and a short-chain dehydrogenase | journal=Proceedings of the National Academy of Sciences | volume=118 | issue=52 | date=2021-12-28 | issn=0027-8424 | pmid=34930840 | pmc=8719858 | doi=10.1073/pnas.2110092118 | page=}}</ref>]]
==Ekstraksi==
Metode [[ekstraksi]] konvensional adalah hidro-distilasi (HD), namun juga dapat diekstraksi dengan ekstraksi [[gelombang mikro]] bebas [[pelarut]] (SFME). Dalam 30 menit, SFME menghasilkan timol dalam jumlah yang sama dengan senyawa teroksigenasi lebih banyak dibandingkan 4,5 jam distilasi hidro pada tekanan atmosfer tanpa memerlukan pelarut.<ref>{{Cite journal |last1=Lucchesi |first1=Marie E |last2=Chemat |first2=Farid |last3=Smadja |first3=Jacqueline |date=2004-07-23 |title=Solvent-free microwave extraction of essential oil from aromatic herbs: comparison with conventional hydro-distillation |url=https://www.sciencedirect.com/science/article/pii/S0021967304008672 |journal=Journal of Chromatography A |volume=1043 |issue=2 |pages=323–327 |doi=10.1016/j.chroma.2004.05.083 |pmid=15330107 |issn=0021-9673}}</ref>
==Kegunaan==
[[File:Thymolum by Danny S. - 001.JPG|thumb|right|Serbuk timol pada kaca arloji]]
Pada tahun 1910an timol merupakan pengobatan pilihan untuk infeksi [[cacing tambang]] di Amerika Serikat.<ref>{{cite book|last=Ferrell|first=John Atkinson|title=The Rural School and Hookworm Disease|url=https://books.google.com/books?id=omYAAAAAYAAJ|series=US Bureau of Education Bulletin|volume=20, Whole No. 593|year=1914|publisher=U.S. Government Printing Office|location=Washington, DC}}</ref><ref name="Rosenau1913">{{cite book|surname=Milton|given=Joseph Rosenau|title=Preventive Medicine and Hygiene|url=https://books.google.com/books?id=mVfQAAAAMAAJ&pg=PA119|year=1913|publisher=D. Appleton|page=119}}</ref> Masyarakat Timur Tengah terus menggunakan [[za'atar]], makanan lezat yang terbuat dari timi dalam jumlah besar, untuk mengurangi dan menghilangkan parasit internal.<ref>{{Cite news|last1=Inskeep|first1=Steve|last2=Godoy|first2=Maria|date=2013-06-11|title=Za'atar: A Spice Mix With Biblical Roots And Brain Food Reputation|language=en|work=NPR|url=https://www.npr.org/sections/thesalt/2013/06/11/190672515/zaatar-a-spice-mix-with-biblical-roots-and-brain-food-reputation|access-date=2022-02-24}}</ref> Ia juga digunakan sebagai [[bahan pengawet]] dalam [[halotana]], anestesi, dan sebagai antiseptik dalam obat kumur. Ketika digunakan untuk mengurangi plak dan radang gusi, timol terbukti lebih efektif bila digunakan dalam kombinasi dengan [[klorheksidin]] dibandingkan jika digunakan sendiri.<ref>{{cite journal | last1 = Filoche | first1 = S. K. | last2 = Soma | first2 = K. | last3 = Sissons | first3 = C. H. | year = 2005 | title = Antimicrobial effects of essential oils in combination with chlorhexidine digluconate | journal = Oral Microbiol. Immunol. | volume = 20 | issue = 4| pages = 221–225 | doi = 10.1111/j.1399-302X.2005.00216.x | pmid = 15943766 }}</ref> Timol juga merupakan bahan antiseptik aktif dalam beberapa pasta gigi. Timol telah berhasil digunakan untuk mengendalikan tungau varroa dan mencegah fermentasi dan pertumbuhan [[kapang]] di koloni lebah.<ref name=bees>{{cite news|last=Ward |first=Mark |date=2006-03-08 |url=http://news.bbc.co.uk/2/hi/science/nature/4780034.stm |title=Almond farmers seek healthy bees |website=BBC News |publisher=BBC}}</ref> Timol juga digunakan sebagai [[pestisida]] yang cepat rusak dan tidak bertahan lama.<ref name="J. Coats 2008"/> Timol juga dapat digunakan sebagai [[disinfektan]] medis dan disinfektan untuk keperluan umum.<ref>{{cite web|url=http://archive.epa.gov/pesticides/reregistration/web/pdf/3143fact.pdf|title=Thymol|publisher=US Environmental Protection Agency|date=September 1993}}</ref> Timol juga digunakan dalam produksi [[mentol]] melalui hidrogenasi cincin aromatik.<ref>{{Cite web |date=2023-10-06 |title=Menthol {{!}} Definition, Structure, & Uses {{!}} Britannica |url=https://www.britannica.com/science/menthol |access-date=2023-10-30 |website=www.britannica.com |language=en}}</ref>
==Daftar tumbuhan yang mengandung timol==
* ''Illicium verum'' ([[bunga lawang]])
* ''Euphrasia rostkoviana''<ref>{{cite journal | pmid = 26000025 | doi=10.1155/2015/734101 | volume=2015 | title=Composition and Antimicrobial Activity of ''Euphrasia rostkoviana'' Hayne Essential Oil | pmc=4427012 | journal=Evid Based Complement Alternat Med | pages=1–5 | last1 = Novy | first1 = P. | last2 = Davidova | first2 = H. | last3 = Serrano Rojero | first3 = C. S. | last4 = Rondevaldova | first4 = J. | last5 = Pulkrabek | first5 = J. | last6 = Kokoska | first6 = L.| year=2015 | doi-access=free }}</ref>
* ''Lagoecia cuminoides''<ref>{{cite journal |doi=10.1080/10412905.1994.9698448 |title=Composition of the Essential Oil of ''Lagoecia cuminoides'' L. from Turkey |year=1994 |last1=Baser |first1=K. H.C. |last2=Tümen |first2=G. |journal=Journal of Essential Oil Research |volume=6 |issue=5 |pages=545–546 }}</ref>
* ''Monarda didyma''<ref>{{cite journal|author1=Donata Ricci|author2=Francesco Epifano|author3=Daniele Fraternale|editor=Olga Tzakou|title=The Essential Oil of Monarda didyma L. (Lamiaceae) Exerts Phytotoxic Activity In Vitro against Various Weed Seeds|journal=Molecules (Basel, Switzerland)|publisher=[[Molecules (journal)|Molecules]]|date=February 2017|volume=22|issue=2|pages=222|pmc=6155892|pmid=28157176|doi=10.3390/molecules22020222|doi-access=free}}</ref>
* ''Monarda fistulosa''<ref>{{cite journal|first1=V. A. |last1=Zamureenko |first2=N. A. |last2=Klyuev |first3=B. V. |last3=Bocharov |first4=V. S. |last4=Kabanov |first5=A. M. |last5=Zakharov |title=An investigation of the component composition of the essential oil of ''Monarda fistulosa'' |journal=Chemistry of Natural Compounds |volume=25 |issue=5 |date=1989 |pages=549–551 |doi=10.1007/BF00598073 |s2cid=24267822 |issn=1573-8388}}</ref>
* ''Mosla chinensis''
* ''Ocimum gratissimum'' ([[selasih mekah]]).<ref>{{Cite journal |last1=Escobar |first1=Angélica |last2=Pérez |first2=Miriam |last3=Romanelli |first3=Gustavo |last4=Blustein |first4=Guillermo |date=2020-12-01 |title=Thymol bioactivity: A review focusing on practical applications |journal=Arabian Journal of Chemistry |volume=13 |issue=12 |pages=9243–9269 |doi=10.1016/j.arabjc.2020.11.009 |issn=1878-5352|doi-access=free |hdl=11336/139451 |hdl-access=free }}</ref>
* ''Origanum compactum''<ref name=ccaa />
* ''Origanum dictamnus''<ref name=lict>{{cite journal
| last1 = Liolios
| first1 = C. C.
| title = Liposomal incorporation of carvacrol and thymol isolated from the essential oil of ''Origanum dictamnus'' L. and in vitro antimicrobial activity
| journal = Food Chemistry
| volume = 112
| issue = 1
| pages = 77–83
| year = 2009
| doi = 10.1016/j.foodchem.2008.05.060
| last2 = Gortzi
| first2 = O.
| last3 = Lalas
| first3 = S.
| last4 = Tsaknis
| first4 = J.
| last5 = Chinou
| first5 = I.}}</ref>
* ''Origanum onites''<ref name=ihte>{{cite journal
| last1 = Ozkan
| first1 = Gulcan
| title = The influence of harvest time on essential oil composition, phenolic constituents and antioxidant properties of Turkish oregano (''Origanum onites'' L.)
| journal = Journal of the Science of Food and Agriculture
| volume = 90
| issue = 2
| pages = 205–209
| year = 2009
| doi = 10.1002/jsfa.3788
| pmid = 20355032
| last2 = Baydar
| first2 = H.
| last3 = Erbas
| first3 = S.}}</ref><ref name=caae>{{cite journal
| last1 = Lagouri
| first1 = Vasiliki
| title = Composition and antioxidant activity of essential oils from Oregano plants grown wild in Greece
| journal = Zeitschrift für Lebensmittel-Untersuchung und -Forschung A
| volume = 197
| issue = 1
| pages = 1431–4630
| year = 1993
| doi = 10.1007/BF01202694
| last2 = Blekas
| first2 = George
| last3 = Tsimidou
| first3 = Maria
| last4 = Kokkini
| first4 = Stella
| last5 = Boskou
| first5 = Dimitrios| s2cid = 81307357
}}</ref>
* ''Origanum vulgare'' ([[oregano]])<ref name=teeo>{{cite journal
| last1 = Kanias
| first1 = G. D.
| title = Trace elements and essential oil composition in chemotypes of the aromatic plant ''Origanum vulgare''
| journal = Journal of Radioanalytical and Nuclear Chemistry
| volume = 227
| issue = 1–2
| pages = 23–31
| year = 1998
| doi = 10.1007/BF02386426
| last2 = Souleles
| first2 = C.
| last3 = Loukis
| first3 = A.
| last4 = Philotheou-Panou
| first4 = E.| s2cid = 94582250
}}</ref><ref name=coeo>{{cite journal
| last1 = Figiel
| first1 = Adam
| title = Composition of oregano essential oil (''Origanum vulgare'') as affected by drying method
| journal = Journal of Food Engineering
| volume = 98
| issue = 2
| pages = 240–247
| year = 2010
| doi = 10.1016/j.jfoodeng.2010.01.002
| last2 = Szumny
| first2 = Antoni
| last3 = Gutiérrez Ortíz
| first3 = Antonio
| last4 = Carbonell Barrachina
| first4 = Ángel A.}}</ref>
* ''Satureja thymbra''
* ''Thymus glandulosus''<ref name=ccaa>{{cite journal
| last1 = Bouchra
| first1 = Chebli
| title = Chemical composition and antifungal activity of essential oils of seven Moroccan Labiatae against ''Botrytis cinerea'' Pers: Fr
| journal = Journal of Ethnopharmacology
| volume = 89
| issue = 1
| pages = 165–169
| year = 2003
| doi = 10.1016/S0378-8741(03)00275-7
| pmid = 14522450
| last2 = Achouri
| first2 = Mohamed
| last3 = Idrissi Hassani
| first3 = L. M.
| last4 = Hmamouchi
| first4 = Mohamed}}</ref>
* ''Thymus hyemalis''<ref name=apth />
* ''Thymus serpyllum''
* ''Thymus praecox''
* ''Thymus vulgaris'' ([[timi biasa]])<ref name=apth>{{cite journal
| last1 = Goodner
| first1 = K.L.
| title = Aromatic profiles of ''Thymus hyemalis'' and Spanish ''T. vulgaris'' essential oils by GC–MS/GC–O
| journal = Industrial Crops and Products
| volume = 24
| issue = 3
| pages = 264–268
| year = 2006
| doi = 10.1016/j.indcrop.2006.06.006
| last2 = Mahattanatawee
| first2 = K.
| last3 = Plotto
| first3 = A.
| last4 = Sotomayor
| first4 = J.
| last5 = Jordán
| first5 = M.}}</ref><ref name=ivcb>{{cite journal
| last1 = Lee
| first1 = Seung-Joo
| title = Identification of volatile components in basil (''Ocimum basilicum'' L.) and thyme leaves (''Thymus vulgaris'' L.) and their antioxidant properties
| journal = Food Chemistry
| volume = 91
| issue = 1
| pages = 131–137
| year = 2005
| doi = 10.1016/j.foodchem.2004.05.056
| last2 = Umano
| first2 = Katumi
| last3 = Shibamoto
| first3 = Takayuki
| last4 = Lee
| first4 = Kwang-Geun}}</ref>
* ''Thymus zygis''<ref name=scet>{{cite journal
| last1 = Moldão Martins
| first1 = M.
| title = Supercritical CO<sub>2</sub> extraction of ''Thymus zygis'' L. subsp. ''sylvestris'' aroma
| journal = The Journal of Supercritical Fluids
| volume = 18
| issue = 1
| pages = 25–34
| year = 2000
| doi = 10.1016/S0896-8446(00)00047-4
| last2 = Palavra
| first2 = A.
| last3 = Beirão da Costa
| first3 = M. L.
| last4 = Bernardo Gil
| first4 = M. G.}}</ref>
* ''Trachyspermum ammi'' ([[Jemuju|ajwain]])
==Toksikologi dan dampak lingkungan==
Pada tahun 2009, [[Badan Perlindungan Lingkungan Amerika Serikat]] (EPA) meninjau literatur penelitian tentang toksikologi dan dampak timol terhadap lingkungan dan menyimpulkan bahwa "timol memiliki potensi toksisitas minimal dan menimbulkan risiko minimal".<ref>{{Federal Register|74|12613}}</ref>
===Kerusakan lingkungan dan penggunaan sebagai pestisida===
Penelitian telah menunjukkan bahwa hidrokarbon [[monoterpena]] dan timol khususnya terdegradasi dengan cepat (DT<sub>50</sub> 16 hari di air, 5 hari di tanah<ref name="J. Coats 2008">{{cite journal|first1=D. |last1=Hu |first2=J. |last2=Coats |title=Evaluation of the environmental fate of thymol and phenethyl propionate in the laboratory |journal=Pest Manag. Sci. |volume=64 |issue=7 |pages=775–779 |date=2008 |doi=10.1002/ps.1555|pmid=18381775 }}</ref>) di lingkungan, dan dengan demikian berisiko rendah karena disipasi cepat dan residu berikatan rendah,<ref name="J. Coats 2008"/> mendukung penggunaan timol sebagai bahan pestisida yang menawarkan alternatif yang aman dibandingkan pestisida kimia lain yang lebih persisten yang dapat tersebar di limpasan dan selanjutnya menghasilkan kontaminasi. Meski demikian, baru-baru ini terdapat penelitian mengenai sistem pelepasan berkelanjutan untuk pestisida yang berasal dari tumbuhan, seperti penggunaan [[polisakarida]] alami yang bersifat [[biodegradasi]] dan [[biokompatibel]].<ref>{{Cite journal |last1=Campos |first1=Estefânia V. R. |last2=Proença |first2=Patrícia L. F. |last3=Oliveira |first3=Jhones L. |last4=Bakshi |first4=Mansi |last5=Abhilash |first5=P. C. |last6=Fraceto |first6=Leonardo F. |date=2019-10-01 |title=Use of botanical insecticides for sustainable agriculture: Future perspectives |url=https://www.sciencedirect.com/science/article/pii/S1470160X18302917 |journal=Ecological Indicators |volume=105 |pages=483–495 |doi=10.1016/j.ecolind.2018.04.038 |issn=1470-160X|hdl=11449/179822 |s2cid=89798604 |hdl-access=free }}</ref>
==Status pelengkap==
* [[Farmakope Britania Raya]]<ref name=ib29>{{cite web
|last = The British Pharmacopoeia Secretariat
|title = Index, BP 2009
|year = 2009
|url = http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
|access-date = 2009-07-05
|url-status = dead
|archive-url = https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
|archive-date = 11 April 2009}}</ref>
* [[Farmakope Jepang]]<ref name=jp15>{{cite web| title =Japanese Pharmacopoeia| url =http://jpdb.nihs.go.jp/jp15e/JP15.pdf| access-date =2010-04-21| url-status =dead| archive-url =https://web.archive.org/web/20110722105441/http://jpdb.nihs.go.jp/jp15e/JP15.pdf| archive-date =22 July 2011}}</ref>
==Referensi==
{{Reflist}}
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