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Anethole

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Anethole
Skeletal formula of anethole
Ball-and-stick model of the anethole molecule
Names
Preferred IUPAC name
1-Methoxy-4-[(E)-prop-1-enyl]benzene[1]
Other names
(E)-1-Methoxy-4-(prop-1-en-1-yl)benzene
(E)-1-Methoxy-4-(1-propenyl)benzene
para-Methoxyphenylpropene
p-Propenylanisole
Isoestragole
trans-1-Methoxy-4-(prop-1-enyl)benzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.914Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+checkY
    Key: RUVINXPYWBROJD-ONEGZZNKSA-NcheckY
  • InChI=1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
    Key: RUVINXPYWBROJD-ONEGZZNKBR
  • O(c1ccc(\C=C\C)cc1)C
Properties
C10H12O
Molar mass 148.205g/mol
Density 0.998 g/cm3
Melting point 20 to 21 °C (68 to 70 °F; 293 to 294 K)
Boiling point 234 °C (453 °F; 507 K)
81 °C (178 °F; 354 K) at 2 mmHg
−9.60×10−5cm3/mol
Hazards
Safety data sheet(SDS) External MSDS
Related compounds
Related compounds
 anisole
estragole
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Anethole(also known asanise camphor)[2]is anorganic compoundthat is widely used as aflavoringsubstance. It is a derivative of thearomaticcompoundallylbenzeneand occurs widely in theessential oilsof plants. It is in the class ofphenylpropanoidorganic compounds. It contributes a large component of the odor and flavor ofaniseandfennel(both in the botanical familyApiaceae),anise myrtle(Myrtaceae),liquorice(Fabaceae), magnolia blossoms, andstar anise(Schisandraceae). Closely related to anethole is itsisomerestragole,which is abundant intarragon(Asteraceae) andbasil(Lamiaceae), and has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid.[clarification needed][3]Anethole is only slightly soluble inwaterbut exhibits high solubility inethanol.This trait causes certain anise-flavoredliqueursto become opaque when diluted with water; this is called theouzo effect.

Structure and production

[edit]

Anethole is an aromatic,unsaturatedetherrelated tolignols.It exists as bothcis–transisomers(see alsoE–Znotation), involving the double bond outside the ring. The more abundant isomer, and the one preferred for use, is thetransorEisomer.[4]

Like related compounds, anethole is poorly soluble in water. Historically, this property was used to detect adulteration in samples.[5]

Most anethole is obtained fromturpentine-like extracts from trees.[3][6]Of only minor commercial significance, anethole can also be isolated from essential oils.[7][8][9]

Essential oil World production Trans-anethole
Anise 8 tonnes (1999) 95%
Star anise 400 tonnes (1999), mostly from China 87%
Fennel 25 tonnes (1999), mostly from Spain 70%

Currently Banwari Chemicals Pvt Ltd situated in Bhiwadi, Rajasthan, India is the leading manufacturer of anethole. It is prepared commercially from 4-methoxypropiophenone,[4][10]which is prepared fromanisole.[3]

Uses

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Flavoring

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Anethole is distinctlysweet,measuring 13 times sweeter thansugar.It is perceived as being pleasant to the taste even at higher concentrations. It is used in alcoholic drinksouzo,rakı,anisetteandabsinthe,among others. It is also used in seasoning and confectionery applications, such as GermanLebkuchen,oral hygiene products, and in small quantities in natural berryflavors.[8]

Precursor to other compounds

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Because theymetabolizeanethole into severalaromatic chemical compounds,some bacteria are candidates for use in commercialbioconversionof anethole to more valuable materials.[11]Bacterial strains capable of using trans-anethole as the sole carbon source include JYR-1 (Pseudomonas putida)[12]and TA13 (Arthrobacter aurescens).[11]

Research

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Antimicrobial and antifungal activity

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Anethole has potentantimicrobialproperties, againstbacteria,yeasts,andfungi.[13]Reported antibacterial properties include bothbacteriostaticandbactericidalaction againstSalmonella enterica[14]but not when used againstSalmonellavia afumigationmethod.[15]Antifungal activity includes increasing the effectiveness of some otherphytochemicals(such aspolygodial) againstSaccharomyces cerevisiaeandCandida albicans;[16]

In vitro,anethole hasantihelminticaction on eggs and larvae of thesheepgastrointestinalnematodeHaemonchus contortus.[17]Anethole also has nematicidal activity against the plant nematodeMeloidogyne javanicain vitro and in pots ofcucumber seedlings.[18]

Insecticidal activity

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Anethole also is a promising insecticide. Several essential oils consisting mostly of anethole haveinsecticidalaction againstlarvaeof themosquitoOchlerotatuscaspius[19]andAedes aegypti.[20][21]In a similar manner, anethole itself is effective against thefungus gnatLycoriella ingenua(Sciaridae)[22]and themold miteTyrophagus putrescentiae.[23]Against the mite, anethole is a slightly more effectivepesticidethanDEET,butanisaldehyde,a related natural compound that occurs with anethole in many essential oils, is 14 times more effective.[23]The insecticidal action of anethole is greater as afumigantthan as a contact agent.trans-Anethole is highly effective as a fumigant against thecockroachBlattella germanica[24]and against adults of theweevilsSitophilus oryzae,Callosobruchus chinensisandbeetleLasioderma serricorne.[25]

As well as an insect pesticide, anethole is an effectiveinsect repellentagainst mosquitos.[26]

Ouzo effect

[edit]
Dilutingabsinthewith water produces a spontaneous microemulsion (ouzo effect)

Anethole is responsible for the "ouzo effect"(also" louche effect "), the spontaneous formation of amicroemulsion[27][28]that gives many alcoholic beverages containing anethole and water their cloudy appearance.[29]Such a spontaneous microemulsion has many potential commercial applications in the food and pharmaceutical industries.[30]

Precursor to illicit drugs

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Anethole is an inexpensive chemical precursor forparamethoxyamphetamine(PMA),[31]and is used in its clandestine manufacture.[32]Anethole is present in the essential oil fromguarana,which has psychoactive effects typically attributed to its caffeine content. The absence of PMA or any other known psychoactive derivative of anethole in human urine after ingestion of guarana leads to the conclusion that any psychoactive effect of guarana is not due to aminated anethole metabolites.[33]

Anethole is also present inabsinthe,aliquorwith a reputation forpsychoactiveeffects; these effects, however, are attributed toethanol.[34](See alsothujone,anethole dithione(ADT), andanethole trithione(ATT).)

Estrogen and prolactin

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Anethole hasestrogenicactivity.[35][36][37]It has been found to significantly increaseuterineweight in immature female rats.[38]

Fennel, which contains anethole, has been found to have agalactagogueeffect in animals. Anethole bears a structural resemblance tocatecholamineslikedopamineand may displace dopamine from its receptors and thereby disinhibitprolactinsecretion, which in turn may be responsible for the galactagogue effects.[39]

Safety

[edit]

In the USA, anethole isgenerally recognized as safe(GRAS). After a hiatus due to safety concerns, anethole was reaffirmed byFlavor and Extract Manufacturers Association(FEMA) as GRAS.[40]The concerns related to liver toxicity and possible carcinogenic activity reported inrats.[41]Anethole is associated with a slight increase inliver cancerin rats,[41]although the evidence is scant and generally regarded as evidence that anethole isnotacarcinogen.[41][42]An evaluation of anethole by theJoint FAO/WHO Expert Committee on Food Additives(JECFA) found its notablepharmacologicproperties to be reduction in motor activity, lowering ofbody temperature,andhypnotic,analgesic,andanticonvulsanteffects.[43]A subsequent evaluation by JECFA found some reason for concern regardingcarcinogenicity,but there is currently insufficient data to support this.[44]At this time, the JECFA summary of these evaluations is that anethole has "no safety concern at current levels of intake when used as a flavoring agent".[45]

In large quantities, anethole is slightlytoxicand may act as an irritant.[46]

History

[edit]

That an oil could be extracted from anise and fennel had been known since theRenaissanceby the German alchemistHieronymus Brunschwig(c. 1450– c. 1512), the German botanistAdam Lonicer(1528–1586), and the German physicianValerius Cordus(1515–1544), among others.[47]Anethole was first investigated chemically by the Swiss chemistNicolas-Théodore de Saussurein 1820.[48]In 1832, the French chemistJean Baptiste Dumasdetermined that the crystallizable components of anise oil and fennel oil were identical, and he determined anethole's empirical formula.[49]In 1845, the French chemistCharles Gerhardtcoined the termanethol– from the Latinanethum(anise) +oleum(oil) – for the fundamental compound from which a family of related compounds was derived.[50]Although the German chemistEmil Erlenmeyerproposed the correct molecular structure for anethole in 1866,[51]it was not until 1872, that the structure was accepted as correct.[47]

See also

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References

[edit]
  1. ^"Anethole".
  2. ^"Anise camphor definition and meaning | Collins English Dictionary".
  3. ^abcFahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst. "Flavors and Fragrances".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a11_141.ISBN978-3527306732.
  4. ^abZhang, Hongwei; Lim, Candy Li-Fen; Zaki, Muhammad; Jaenicke, Stephan; Chuah, Gaik Khuan (2018)."A Dual-Functional Catalyst for Cascade Meerwein–Pondorf–Verley Reduction and Dehydration of 4′-Methoxypropiophenone to Anethole".ChemSusChem.11(17): 3007–3017.doi:10.1002/cssc.201801340.ISSN1864-564X.PMID29927044.S2CID49342669.
  5. ^Waldbott, S. (1920)."Essential oils".Chemical Abstracts.14(17): 3753–3755.
  6. ^US 4902850,Davis, Curry B., "Purification of anethole by crystallization", issued 1990-02-20
  7. ^Chopra, R. N.; Chopra, I. C.; Handa, K. L.; Kapur, L. D. (1958).Chopra's Indigenous Drugs of India(2nd ed.). Academic Publishers. pp. 178–179.ISBN978-81-85086-80-4.
  8. ^abAshurst, Philip R. (1999).Food Flavorings.Springer. p. 460.ISBN978-0-8342-1621-1.[permanent dead link]
  9. ^Bodsgard, B. R.; Lien, N. R.; Waulters, Q. T. (2016). "Liquid CO2Extraction and NMR Characterization of Anethole from Fennel Seed: A General Chemistry Laboratory ".Journal of Chemical Education.93(2): 397–400.Bibcode:2016JChEd..93..397B.doi:10.1021/acs.jchemed.5b00689.
  10. ^Zhang, Hongwei; Quek, Zhan Jiang; Jaenicke, Stephan; Chuah, Gaik-Khuan (2021-08-01)."Hydrophobicity and co-solvent effects on Meerwein-Ponndorf-Verley reduction/dehydration cascade reactions over Zr-zeolite catalysts".Journal of Catalysis.400:50–61.doi:10.1016/j.jcat.2021.05.011.ISSN0021-9517.S2CID236342527.
  11. ^abShimoni, E; Baasov, T.; Ravid, U.; Shoham, Y. (2002)."Thetrans-anethole degradation pathway in anArthrobactersp ".Journal of Biological Chemistry.277(14): 11866–11872.doi:10.1074/jbc.M109593200.PMID11805095.
  12. ^Ryu, J.; Seo, J.; Lee, Y.; Lim, Y.; Ahn, J. H.; Hur, H. G. (2005). "Identification ofsyn- andanti-anethole-2,3-epoxides in the metabolism oftrans-anethole by the newly isolated bacteriumPseudomonas putidaJYR-1 ".Journal of Agricultural and Food Chemistry.53(15): 5954–5958.doi:10.1021/jf040445x.PMID16028980.
  13. ^De, M.; De, A. K.; Sen, P.; Banerjee, A. B. (2002). "Antimicrobial properties of star anise (Illicium verumHook. f.) ".Phytotherapy Research.16(1): 94–95.doi:10.1002/ptr.989.PMID11807977.S2CID27196549.
  14. ^Kubo, I.; Fujita, K. (2001). "Naturally occurring anti-Salmonellaagents ".Journal of Agricultural and Food Chemistry.49(12): 5750–5754.doi:10.1021/jf010728e.PMID11743758.
  15. ^Weissinger, W. R.; McWatters, K. H.; Beuchat, L. R. (April 2001)."Evaluation of volatile chemical treatments for lethality toSalmonellaon alfalfa seeds and sprouts ".Journal of Food Protection.64(4): 442–450.doi:10.4315/0362-028X-64.4.442.PMID11307877.
  16. ^Fujita, K.; Fujita, T.; Kubo, I. (2007)."Anethole, a potential antimicrobial synergist, converts a fungistatic dodecanol to a fungicidal agent".Phytotherapy Research.21(1): 47–51.doi:10.1002/ptr.2016.PMID17078111.S2CID9666596.
  17. ^Camurça-Vasconcelos, A. L.; Bevilaqua, C. M.; Morais, S. M.; Maciel, M. V.; Costa, C. T.; Macedo, I. T.; Oliveira, L. M.; Braga, R. R.; Silva, R. A.; Vieira, L. S. (2007). "Anthelmintic activity ofCroton zehntneriandLippia sidoidesessential oils ".Veterinary Parasitology.148(3–4): 288–294.doi:10.1016/j.vetpar.2007.06.012.PMID17629623.
  18. ^Oka, Y.; Nacar, S.; Putievsky, E.; Ravid, U.; Yaniv, Z.; Spiegel, Y. (2000)."Nematicidal activity of essential oils and their components against the root-knot nematode".Phytopathology.90(7): 710–715.doi:10.1094/PHYTO.2000.90.7.710.PMID18944489.
  19. ^Knio, K. M.; Usta, J.; Dagher, S.; Zournajian, H.; Kreydiyyeh, S. (2008). "Larvicidal activity of essential oils extracted from commonly used herbs in Lebanon against the seaside mosquito,Ochlerotatus caspius".Bioresource Technology.99(4): 763–768.Bibcode:2008BiTec..99..763K.doi:10.1016/j.biortech.2007.01.026.PMID17368893.
  20. ^Cheng, S. S.; Liu, J. Y.; Tsai, K. H.; Chen, W. J.; Chang, S. T. (2004). "Chemical composition and mosquito larvicidal activity of essential oils from leaves of differentCinnamomum osmophloeumprovenances ".Journal of Agricultural and Food Chemistry.52(14): 4395–4400.doi:10.1021/jf0497152.PMID15237942.
  21. ^Morais, S. M.; Cavalcanti, E. S.; Bertini, L. M.; Oliveira, C. L.; Rodrigues, J. R.; Cardoso, J. H. (2006). "Larvicidal activity of essential oils from BrazilianCrotonspecies againstAedes aegyptiL. ".Journal of the American Mosquito Control Association.22(1): 161–164.doi:10.2987/8756-971X(2006)22[161:LAOEOF]2.0.CO;2.PMID16646345.S2CID33429927.
  22. ^Park, I. K.; Choi, K. S.; Kim, D. H.; Choi, I. H.; Kim, L. S.; Bak, W. C.; Choi, J. W.; Shin, S. C. (2006). "Fumigant activity of plant essential oils and components from horseradish (Armoracia rusticana), anise (Pimpinella anisum) and garlic (Allium sativum) oils againstLycoriella ingenua(Diptera: Sciaridae) ".Pest Management Science.62(8): 723–728.doi:10.1002/ps.1228.PMID16786497.
  23. ^abLee, H. S. (2005)."Food protective effect of acaricidal components isolated from anise seeds against the stored food mite,Tyrophagus putrescentiae(Schrank) ".Journal of Food Protection.68(6): 1208–1210.doi:10.4315/0362-028X-68.6.1208.PMID15954709.
  24. ^Chang, K. S.; Ahn, Y. J. (2002). "Fumigant activity of (E)-anethole identified inIllicium verumfruit againstBlattella germanica".Pest Management Science.58(2): 161–166.doi:10.1002/ps.435.PMID11852640.
  25. ^Kim, D. H.; Ahn, Y. J. (2001). "Contact and fumigant activities of constituents ofFoeniculum vulgarefruit against three coleopteran stored-product insects ".Pest Management Science.57(3): 301–306.doi:10.1002/ps.274.PMID11455661.
  26. ^Padilha de Paula, J.; Gomes-Carneiro, M. R.; Paumgartten, F. J. (2003). "Chemical composition, toxicity and mosquito repellency ofOcimum selloioil ".Journal of Ethnopharmacology.88(2–3): 253–260.doi:10.1016/s0378-8741(03)00233-2.PMID12963152.
  27. ^Sitnikova, Natalia L.; Sprik, Rudolf; Wegdam, Gerard; Eiser, Erika (2005)."Spontaneously formedtrans-anethol/water/alcohol emulsions: Mechanism of formation and stability "(PDF).Langmuir.21(16): 7083–7089.doi:10.1021/la046816l.PMID16042427.Archived fromthe original(PDF)on 2009-03-18.Retrieved2009-03-15.
  28. ^Carteau, David; Bassani, Dario; Pianet, Isabelle (2008)."The" Ouzo effect ": Following the spontaneous emulsification oftrans-anethole in water by NMR ".Comptes Rendus Chimie.11(4–5): 493–498.doi:10.1016/j.crci.2007.11.003.
  29. ^Sánchez Domínguez, M.; Rodríguez Abreu, C. (2016).Nanocolloids: A Meeting Point for Scientists and Technologists.Elsevier Science. p. 369.ISBN978-0-12-801758-6.Retrieved2018-08-02.O/W and W/O nano-emulsions can also be formed without a surfactant by self-emulsification, using the so-called Ouzo effect. The major components of Ouzo (a Greek drink) aretrans-anethole, ethanol, and water. Anethole is almost insoluble...
  30. ^Spernath, A.; Aserin, A. (2006). "Microemulsions as carriers for drugs and nutraceuticals".Advances in Colloid and Interface Science.128–130: 47–64.doi:10.1016/j.cis.2006.11.016.PMID17229398.
  31. ^Waumans, D.; Bruneel, N.; Tytgat, J. (2003). "Anise oil aspara-methoxyamphetamine (PMA) precursor ".Forensic Science International.133(1–2): 159–170.doi:10.1016/S0379-0738(03)00063-X.PMID12742705.
  32. ^Waumans, D.; Hermans, B.; Bruneel, N.; Tytgat, J. (2004). "A neolignan-type impurity arising from the peracid oxidation reaction of anethole in the surreptitious synthesis of 4-methoxyamphetamine (PMA)".Forensic Science International.143(2–3): 133–139.doi:10.1016/j.forsciint.2004.02.033.PMID15240033.
  33. ^Benoni, H.; Dallakian, P.; Taraz, K. (1996). "Studies on the essential oil from guarana".Zeitschrift für Lebensmittel-Untersuchung und -Forschung.203(1): 95–98.doi:10.1007/BF01267777.PMID8765992.S2CID45636969.
  34. ^Lachenmeier, D. W. (2008). "Thujon-Wirkungen von Absinth sind nur eine Legende—Toxikologie entlarvt Alkohol als eigentliche Absinthismus-Ursache" [Thujone-attributable effects of absinthe are only an urban legend—toxicology uncovers alcohol as real cause of absinthism].Medizinische Monatsschrift für Pharmazeuten(in German).31(3): 101–106.PMID18429531.
  35. ^Jordan, Virgil Craig (1986).Estrogen/Antiestrogen Action and Breast Cancer Therapy.University of Wisconsin Press. pp. 21–22.ISBN978-0-299-10480-1.
  36. ^Howes, M.-J. R.; Houghton, P. J.; Barlow, D. J.; Pocock, V. J.; Milligan, S. R. (November 2002)."Assessment of estrogenic activity in some common essential oil constituents".The Journal of Pharmacy and Pharmacology.54(11): 1521–1528.doi:10.1211/002235702216.ISSN0022-3573.PMID12495555.S2CID28650422.
  37. ^Albert-Puleo, M. (December 1980)."Fennel and anise as estrogenic agents".Journal of Ethnopharmacology.2(4): 337–344.doi:10.1016/s0378-8741(80)81015-4.ISSN0378-8741.PMID6999244.
  38. ^Tisserand, Robert; Young, Rodney (2013).Essential Oil Safety: A Guide for Health Care Professionals.Elsevier Health Sciences. p. 150.ISBN978-0-7020-5434-1.
  39. ^Bone, Kerry; Mills, Simon Y. (2013).Principles and Practice of Phytotherapy.Modern Herbal Medicine. Vol. 2. Elsevier Health Sciences. p. 559.ISBN978-0-443-06992-5.
  40. ^Newberne, P.; Smith, R. L.; Doull, J.; Goodman, J. I.; Munro, I. C.; Portoghese, P. S.; Wagner, B. M.; Weil, C. S.; Woods, L. A.; Adams, T. B.; Lucas, C. D.; Ford, R. A. (1999). "The FEMA GRAS assessment oftrans-anethole used as a flavouring substance. Flavour and Extract Manufacturers' Association ".Food and Chemical Toxicology.37(7): 789–811.doi:10.1016/S0278-6915(99)00037-X.PMID10496381.
  41. ^abcNewberne, P. M.; Carlton, W. W.; Brown, W. R. (1989). "Histopathological evaluation of proliferative liver lesions in rats fed trans-anethole in chronic studies".Food and Chemical Toxicology.27(1): 21–26.doi:10.1016/0278-6915(89)90087-2.PMID2467866.
  42. ^Waddell, W. J. (2002)."Thresholds of carcinogenicity of flavors".Toxicological Sciences.68(2): 275–279.doi:10.1093/toxsci/68.2.275.PMID12151622.
  43. ^Joint FAO/WHO Expert Committee on Food Additives."trans-Anethole ".WHO Food Additives Series. International Program on Chemical Safety (IPCS).
  44. ^Joint FAO/WHO Expert Committee on Food Additives (1998)."trans-Anethole ".WHO Food Additives Series. International Program on Chemical Safety (IPCS).
  45. ^"Summary of Evaluations Performed by the Joint FAO/WHO Expert Committee on Food Additives:trans-Anethole ".International Program on Chemical Safety (IPCS). 2001-11-12.Archivedfrom the original on 2009-03-11.Retrieved2009-03-10.
  46. ^"Safety data for anethole".Physical & Theoretical Chemistry Laboratory Safety, Oxford University. Archived fromthe originalon 2008-06-15.Retrieved2009-03-10.
  47. ^abSee:
  48. ^De Saussure, N.-T. (1820)."Observations sur la combinaison de l'essence de citron avec l'acide muriatique, et sur quelques substances huileuses"[Observations on the combination of lemon essence with muriatic acid, and on several oily substances].Annales de Chimie et de Physique.Série 2 (in French).13:259–284.See especially pp. 280–284.
  49. ^See:
    • Dumas, J. (1832)."Mémoire sur les substances végétales qui se rapprochent du camphre, et sur quelques huiles essentielles"[Memoir on plant substances that resemble camphor, and on several essential oils].Annales de Chimie et de Physique.Série 2 (in French).50:225–240.On p. 234, Dumas provides anempirical formulaC10H6O⁠1/2⁠for anethol. If the subscripts are doubled and if the subscript for carbon is then halved (because Dumas, like many of his contemporaries, used the wrongatomic massfor carbon, 6 instead of 12), then Dumas' empirical formula is correct.
    • Dumas' finding that the crystallizable components of anise oil and fennel oil were identical was confirmed in 1833 by the team of Rodolphe Blanchet (1807–1864) and Ernst Sell (1808–1854). See:Blanchet, Sell (1833)."Ueber die Zusammensetzung einiger organischer Substanzen"[On the composition of some organic substances].Annalen der Pharmacie(in German).6(3): 259–313.doi:10.1002/jlac.18330060304.See especially pp. 287–288.
    • Dumas' empirical formula for anethole was confirmed in 1841 by the French chemistAuguste Cahours.See:Cahours, A. A. T. (1841)."Sur les essences de fenouil, de badiane et d'anis"[On the essential oils of fennel, star anise, and anise].Annales de Chimie et de Physique.Série 3 (in French).2:274–308.See pp. 278–279. Note that the subscripts of Cahours' empirical formula (C40H24O2) must be divided by 2 and then the subscript for carbon must be divided again by 2 (because, like many chemists of his time, Cahours used the wrong atomic mass for carbon, 6 instead of 12). If these changes are made, the resulting empirical formula is correct.
  50. ^Gerhardt, Charles (1845)."Ueber die Identität des Dragonöls und des Anisöls"[On the identity of tarragon oil and anise oil].Journal für praktische Chemie(in German).36:267–276.doi:10.1002/prac.18450360159.[From p. 269:] Ich werde keinen neuen Namen für jede einzelne Art der folgenden physisch verschiedenen Arten annehmen. In meinem Werke bezeichne ich sie als Varietäten der Gattung „Anethol ".[I will adopt no new name for any individual species of the following physically different species. In my work, I designate them as varieties of the genusanethol.]
  51. ^Erlenmeyer, Emil (1866)."Ueber die Constitution des Anisols (Anethols)"[On the constitution of anisol (anethol)].Zeitschrift für Chemie.2nd Series (in German).2:472–474.
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