Skip to main content
SpringerLink
Log in

Aroma Composition of Aniseed and Aniseed-Flavored Beverages

  • Living reference work entry
  • First Online:
Natural Products in Beverages

Part of the book series: Reference Series in Phytochemistry ((RSP))

  • 36 Accesses

Abstract

Pimpinella anisum L. is an aromatic plant that has been used in the human diet for thousands of years in the flavoring of food and alcoholic beverages, as well as in pharmacy, especially in the Mediterranean basin. The most important feature of aniseed is that it has an essential oil containing very special and strong aroma compounds. Aniseed aroma components are extracted mainly through hydro-distillation or steam-distillation before the GC-MS technique is applied. Aroma components of the aniseed and aniseed flavored alcoholic beverages can be mainly classified under the monoterpenes, sesquiterpenes, and phenylpropanoids groups. The majority of aniseed oil consists of transanethol, estragol, γ-himachalene, α-zingiberene, and p-anisaldehyde, which all have distinct sweet, mastic, anise, herbal, and bitter almond aromas. Trace aroma compounds of aniseed include α-pinene, limonene, p-cymene, γ-terpinene, α-terpinene, cis-anethole, methyl eugenol, germacrene-D, and β-bisabolen, which have a significant effect on the final product. Aniseed or aniseed flavor is applied in the production of a variety of distilled alcoholic beverages throughout the world. Notable ones include rakı in Türkiye, ouzo and tsipouro in Greece, janezevec in Slovenia, pastis in France, sambuca in Italy, cazalla, pacharán, and chinchon in Spain, and arak in Lebanon and Syria. Transanethole, estragole, cis-anethole, himachelene, p-anisaldehyde, and linalool are the dominant aroma compounds in all anise-flavored alcoholic beverages, which have characteristics that can be described as spicy, anise, mastic, sweet, and resinous odors.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Abbreviations

DA:

Descriptive analysis

EOs:

Essential oils

GC/MS:

Gas chromatography/Mass spectrometry

SFE:

Supercritical fluid extraction

SPME:

Solid phase microextraction

UAE:

Ultrasound-assisted extraction

VMHD:

Vacuum microwave hydro-distillation

References

  1. Davis PH (1972) Flora of Turkey and the East Aegean Islands, 4th edn. Edinburgh University Press, Edinburgh

    Google Scholar 

  2. Heeger EF (1956) Handbuch des arznei- und gewürzpfl anzenbaues drogengewinnung. Deutscher Bauernverlag, Berlin

    Google Scholar 

  3. Özgüven M (2001) Aniseed. In: Peter KV (ed) Handbook of herbs and spices, 2nd edn. Woodhead Publishing, Cambridge

    Google Scholar 

  4. Tainter DR, Grenis AT (1993) Spices and seasonings: a food technology handbook. VCH Publishers, Weinheim

    Google Scholar 

  5. Simon JE, Chadwick AF, Craker LE (1984) Herbs: an indexed bibliography 1971–1980, the scientific literature on selected herbs, and aromatic and medicinal plants of the temperate zone. Archon Books, Hamden

    Google Scholar 

  6. Christaki E, Bonos E, Giannenas I, Florou-Paneri P (2012) Aromatic plants as a source of bioactive compounds. Agriculture 2:228–243

    Article  Google Scholar 

  7. Tonutti I, Liddle P (2010) Aromatic plants in alcoholic beverages. A review. Flavour Fragr J 25:341–350

    Article  CAS  Google Scholar 

  8. Leal PF, Almeida TS, Prado GH, Prado JM, Meireles MA (2011) Extraction kinetics and anethole content of fennel (Foeniculum vulgare) and anise seed (Pimpinella anisum) extracts obtained by soxhlet, ultrasound, percolation, centrifugation, and steam distillation. Sep Sci Technol 46:1848–1856

    Article  CAS  Google Scholar 

  9. Ozcan K (2021) Anason (Pimpinella anisum L.) tohumunun uçucu yağı ve aroma bileşimi üzerine yörenin etkisi. Dissertation, Universitiy of Çukurova

    Google Scholar 

  10. Samojlik I, Mijatovic V, Petkovic S, Skrbic B, Bozin B (2012) The ınfluence of essential oil of aniseed (Pimpinella anisum L.) on drug effects on the central nervous system. Fitoterapia 83:1466–1473

    Article  CAS  PubMed  Google Scholar 

  11. Odeh A, Allaf AW (2017) Determination of polyphenol component fractions and integral antioxidant capacity of Syrian aniseed and fennel seed extracts using GC–MS, HPLC analysis, and photochemiluminescence assay. Chem Pap 71(9):1731–1737

    Article  CAS  Google Scholar 

  12. Ullah H, Athar M, Ijaz M, Tadesse B, Honermeir B (2013) Evaluation of anise (Pimpinella anisum L.) accessions with regard to morphological characteristics, fruit yield, oil contents and composition. J Med Plant Res 7(29):2177–2186

    Article  CAS  Google Scholar 

  13. Arslan N, Gürbüz B, Sarıhan EO, Bayrak A, Gümüşçü A (2004) Variation in essential oil content and composition in Turkish anise (Pimpinella anisum l.) populations. Turk J Agric For 28:173–177

    CAS  Google Scholar 

  14. Tavallali V, Zareiyan F (2018) Antioxidant activity, polyphenolic contents and essential oil composition of aniseed (Pimpinella anisum L.) as influenced by 5-aminolevulinic acid. J Food Meas Charact 12(2):1065–1071

    Article  Google Scholar 

  15. Ribéreau-Gayon P, Gloires Y, Maujean A, Dubourdieu D (2006) The chemistry of wine and stabilization and treatments. In: Handbook of enology, vol 2. Wiley, Chichester

    Google Scholar 

  16. Zhang H, Stephanopoulos G (2016) Co-culture engineering for microbial biosynthesis of 3-amino-benzoic acid in Escherichia coli. Biotechnol J 11:981–987

    Article  CAS  PubMed  Google Scholar 

  17. Shin YJ, Jung MJ, Kim NS, Kim K, Lee DS (2007) Characterization of fennel flavors by solid phase trapping-solvent extraction and gas chromatography-mass spectrometry. Bull Korean Chem Soc 28(12):2389–2395

    Article  CAS  Google Scholar 

  18. Zeller A, Rychlik M (2007) Impact of estragole and other odorants on the flavour of anise and tarragon. Flavour Fragr J 22:105–113

    Article  CAS  Google Scholar 

  19. Acimovic M, Oljaca S, Tesevic V, Todosijevic M, Djisalov J (2015) Compositional characteristics of the essential oil of pimpinella anisum and foeniculum vulgare grown in Serbia. Bot Serbica 39(1):09–14

    Google Scholar 

  20. Burdock AG (2005) Fenaroli’s handbook of flavor ingredients, 5th edn. Boca Raton, CRC Press

    Google Scholar 

  21. Diaz-Maroto MC, Diaz-Maroto Hidalgo IJ, Sanchez-Palomo E, Perez-Coello MS (2005) Volatile components and key odorants of fennel (Foeniculum vulgare Mill.) and thyme (Thymus vulgaris l.) oil extracts obtained by simultaneous distillation – extraction and supercritical fluid extraction. J Agric Food Chem 53(13):5385–5389

    Article  CAS  PubMed  Google Scholar 

  22. Dağıstanlıoğlu C, Kaymak S, Uçgun K, Atasay A (2009) Göller Bölgesi’nde seçilmiş bazı anason populasyonlarının verim ve kalite özellikleri üzerine araştırmalar. Selçuk Tarım ve Gıda Bilimleri Dergisi 23(47):38–43

    Google Scholar 

  23. Skalicka-Wozniak K, Walasek M, Ludwiczuk A, Glowniak K (2013) Isolation of terpenoids from Pimpinella anisum essential oil by high-performance counter-current chromatography. J Sep Sci 36:2611–2614

    Article  CAS  PubMed  Google Scholar 

  24. Darıcı M, Bergama D, Cabaroglu T (2019) Effect of triple pot still distillation on the volatile compositions during the Rakı production. J Food Process Preserv 43(6):e13864

    Article  Google Scholar 

  25. Awouafack MD, Tane P, Kuete V, Eloff JN (2013) Sesquiterpenes from the medicinal plants of Africa. In: Kuete V (ed) Medicinal plant research in Africa. Elsevier, Oxford

    Google Scholar 

  26. Orav A, Raal A, Arak E (2008) Essential oil composition of Pimpinella anisum L. fruits from various European countries. Nat Prod Res 22(3):227–232

    Article  CAS  PubMed  Google Scholar 

  27. Luís N, Sousa S, Wackerlig J, Dobusch D, Duarte AP, Pereira L, Domingues F (2019) Star anise (Illicium verum Hook. f.) essential oil: antioxidant properties and antibacterial activity against Acinetobacter baumannii. Flavour Fragr J 34(4):260–270

    Article  Google Scholar 

  28. Huang B, Liang J, Wang G, Qin L (2012) Comparison of the volatile components of Illicium verum and I. lanceolatum from East China. J Essent Oil Bear Plants 15(3):467–475

    Article  CAS  Google Scholar 

  29. Vella FM, Calandrelli R, Cautela D, Fiume I, Pocsfalvi G, Laratta B (2020) Chemometric screening of fourteen essential oils for their composition and biological properties. Molecules 25(21):5126

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Cvetkovic D, Stanojevic J, Djordjevic N, Karabegović I, Stanojevic L et al (2022) Effect of different extraction techniques on the composition of essential oil isolated from fennel (Foeniculum vulgare mill.) rhizome. J Essent Oil Res:1–11

    Google Scholar 

  31. Boelens MA (1991) Spices and condiments II. In: Maarse H (ed) Volatile compounds in food and beverages. Marcel Dekker Inc, New York/Basel

    Google Scholar 

  32. Minodier P, Pommier P, Moulène E, Retornaz K, Prost N et al (2003) Intoxication aiguë par la badiane chez le nourrisson. Arch Pediatr 10(7):619–621

    Article  CAS  PubMed  Google Scholar 

  33. Madden GR, Schmitz KH, Fullerton KA (2012) Case of infantile star anise toxicity. Pediatr Emerg Care 28(3):284–285

    Article  PubMed  Google Scholar 

  34. Kakemoto E, Okuyama E, Nagata K, Ozoe Y (1999) Interaction of anisatin with rat brain γ-aminobutyric acid receptors: allosteric modulation by competitive antagonists. Biochem Pharmacol 58:617–621

    Article  CAS  PubMed  Google Scholar 

  35. Santana ACMD, Uetenabaro APT, Silva TMDBE, Costa LCDB, Oliveira RAD (2016) Storage conditions of Ocimum gratissimum L. leaves influence the quality of essential oil. J Essent Oil Res 29(1):56–63

    Article  Google Scholar 

  36. Mahmoodi Sourestani M, Malekzadeh M, Tava A (2014) Influence of drying, storage and distillation times on essential oil yield and composition of anise hyssop [Agastache foeniculum(Pursh.) Kuntze]. J Essent Oil Res 26(3):177–184

    Article  CAS  Google Scholar 

  37. Díaz-Maroto MC, Pérez-Coello MS, González Viñas MA, Cabezudo MD (2003) Influence of drying on the flavor quality of spearmint (Mentha spicata L.). J Agric Food Chem 51(5):1265–1269

    Article  PubMed  Google Scholar 

  38. Schweiggert U, Carle R, Schieber A (2007) Conventional and alternative processes for spice production, a review. Trends Food Sci Technol 18:260–268

    Article  CAS  Google Scholar 

  39. Kavoosi G, Rowshan V (2013) Chemical composition, antioxidant and antimicrobial activities of essential oil obtained from Ferula assa-foetida oleogum-resin: effect of collection time. Food Chem 138:2180–2187

    Article  CAS  PubMed  Google Scholar 

  40. Jesus AS, Blank AF, Alves MF, Arrigoni-Blank MF, Lima RN et al (2016) Influence of storage time and temperature on the chemical composition of the essential oil of Hyptis pectinata L. Poit Revista Brasileira de Plantas Medicinais 18:336–340

    Article  CAS  Google Scholar 

  41. Cooksey K (2006) Food packaging, principles and practices. In: Robertson G (ed) Packaging technology and science, 2nd edn. CRC, Taylor and Francis, Boca Raton

    Google Scholar 

  42. Masand S, Madan S, Balian SK (2014) Modern concept of storage and packaging of raw herbs used in ayurveda. Int J Res Ayurveda Pharm 5(2):242–245

    Article  Google Scholar 

  43. Lisboa CF, Melo EC, Sperotto NCZ, Ávila MBR, da Silva LC et al (2022) Packaging and storage of medicinal plants. Res Soc Dev 11(7)

    Google Scholar 

  44. García D, Pupo S, Crespo M, Fuentes L (1998) Estudio farmacognóstico de Ocimum gratissimum L (Orégano cimarrón) /Pharmacognostic study of Ocimum gratissimum (Oregano cimarrón). Revista Cubana Plantas Medicinales 3(1):31–36

    Google Scholar 

  45. Chaliha M, Cusack A, Currie M, Sultanbawa Y, Smyth H (2013) Effect of packaging materials and storage on major volatile compounds in three Australian native herbs. J Agric Food Chem 61(24):5738–5745

    Article  CAS  PubMed  Google Scholar 

  46. Gerogiannaki M, Masouras T (2015) Composition of transanethol and other aromatic volatiles in anisated alcoholic beverage by head-space gc-ms chromatography. Paper presented at the 25th international scientific-experts congress on agriculture and food industry, University of Ege, İzmir, 25–27 September 2014

    Google Scholar 

  47. Cabaroglu T, Darıcı M, Erten H (2020) Rakı teknolojisi ve diğer distile içkilerin üretimi. In: Erkmen O, Erten H, Sağlam H (eds) fermente ürünler teknolojisi ve mikrobiyolojisi, 1st edn. Nobel Akademik Yayıncılık, Ankara

    Google Scholar 

  48. European Union Regulation (2019) Regulation (EC) No 2019/787 of the European Parliament and of the Council of 17 April 2019 on the definition, description, presentation and labelling of spirit drinks, the use of the names of spirit drinks in the presentation and labelling of other foodstuffs, the protection of geographical indications for spirit drinks, the use of ethyl alcohol and distillates of agricultural origin in alcoholic beverages, and repealing Regulation (EC) No 110/2008. https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32019R0787

  49. Cabaroglu T, Yilmaztekin M (2011) Methanol and major volatile compounds of Turkish Raki and effect of distillate source. J Inst Brew 117:98–105

    Article  CAS  Google Scholar 

  50. Yilmaztekin M, Cabaroglu T, Gunata Z (2011) Differentiation of Turkish Rakies through headspace solid-phase microextraction and gas chromatography-mass spectrometry analysis. J Inst Brew 117(4):622–626

    Article  CAS  Google Scholar 

  51. Karapanagioti HK, Bekatorou A (2014) Alcohol and dilution water characteristics in distilled anis (ouzo). J Agric Food Chem 62(21):4932–4937

    Article  CAS  PubMed  Google Scholar 

  52. Buglass AJ, McKay M, Lee CG (2011) Distilled spirits. In: Buglass AJ (ed) Handbook of alcoholic beverages: technical, analytical and nutritional aspects, 1st edn. Wiley, Chichester

    Chapter  Google Scholar 

  53. Protected Designation of Origin (Ouzo) 2016 geographıcal indication ouzo of thrace. No: PGI-GR-01841

    Google Scholar 

  54. Zabetakis I (2012) Anise spirits: types, sensory properties and sensory analysis. In: Piggot J (ed) Alcoholic beverages. Woodhead Publishing Limited, Oxford

    Google Scholar 

  55. Zat E (2018) Rakı Ansiklopedisi, Istanbul

    Google Scholar 

  56. Karaveli M (1970) Rakı ve Damıtma Teknolojisi, Tekel Genel Müdürlüğü

    Google Scholar 

  57. Turkish Patent Institute (2009) Rakı- Distilled alcoholic beverages, certificate of registry on the protected designation of origin of the product (No: 136), 8 December 2009. Official Journal of Turkey No. 27426 Ankara, Turkey

    Google Scholar 

  58. Anli RE, Bayram M (2010) Traditional aniseed-flavored spirit drinks. Food Rev Intl 26(3):246–269

    Article  CAS  Google Scholar 

  59. Ozkandan S, Cabaroglu T (2012) Determination of main volatile compounds in different type of Turkish Rakies by gas Chromatography with direct injectıon method (in Turkish). J Food 37:87–94

    Google Scholar 

  60. Darıcı M, Ozcan K, Beypınar D, Cabaroglu T (2021) Sensory lexicon and major volatiles of rakı using descriptive analysis and gc-fid/ms. Foods 10(7):1494

    Article  PubMed  PubMed Central  Google Scholar 

  61. Geahchan A, Khalife C, Chambon P, Chambon R (1991) Analysis of anisated fermented grape distillates by gas-liquid chromatography. J Food Compos Anal 4(4):304–314

    Article  CAS  Google Scholar 

  62. Jurado J, Ballesteros O, Alcazar A, Pablos F, Martin M et al (2007) Characterization of aniseed-flavoured spirit drinks by headspace solid-phase microextraction gas chromatography–mass spectrometry and chemometrics. Talanta 72(2):506–511

    Article  CAS  PubMed  Google Scholar 

  63. Kontominas MG (1986) Volatile constituents of Greek ouzo. J Agric Food Chem 34(5):847–849

    Article  CAS  Google Scholar 

  64. Lawless HT, Heymann H (2010) Sensory evaluation of food: principles and practices, 2nd edn. Springer Science & Business Media, New York

    Book  Google Scholar 

  65. Lawless L, Civille G (2013) Developing lexicons: a review. J Sens Stud 28:270–281

    Article  Google Scholar 

  66. Noble AC, Arnold RA, Masuda BM, Pecore SD, Schmidt JO et al (1984) Progress towards a standardized sys-tem of wine aroma terminology. Am J Enol Vitic 35:107–109

    Article  Google Scholar 

  67. Noble AC, Arnold RA, Buechsenstein J, Leach EJ, Schmidt JO et al (1987) Modification of a standardized system of wine aroma terminology. Am J Enol Vitic 38:143–146

    Article  Google Scholar 

  68. Shortreed GW, Richards P, Swan JS, Burtles S (1979) The flavor terminology of scotch whisky. Brewers Guardian Nov 58–62

    Google Scholar 

  69. Bordeu E, Formas G, Agosin E (2004) Proposal for a standardized set of sensory terms for pisco, a young Muscat wine distillate. Am J Enol Vitic 55:104–107

    Article  Google Scholar 

  70. Tsachaki M, Arnaoutopoulou AP, Margomenou L, Roubedakis SC, Zabetakis I (2010) Development of a suitable lexicon for sensory studies of the anise-flavoured spirits ouzo and tsipouro. Flavour Fragr J 25(6):468–474

    Article  CAS  Google Scholar 

  71. El Asbahani A, Miladi K, Badri W, Sala M, Addi EHA et al (2015) Essential oils: from extraction to encapsulation. Int J Pharm 483:220–243

    Article  CAS  PubMed  Google Scholar 

  72. Haro-González JN, Castillo-Herrera GA, Martínez-Velázquez M, Espinosa-Andrews H (2021) Clove essential oil (syzygium aromaticum l. myrtaceae): extraction, chemical composition, food applications, and essential bioactivity for human health. Molecules 26:6387

    Article  PubMed  PubMed Central  Google Scholar 

  73. Saibi S, Belhadj M, Benyoussef EH (2012) Essential oil composition of pimpinella anisum from Algeria. Anal Chem Lett 2(6):401–404

    Article  CAS  Google Scholar 

  74. Fernández-García T, Martín ME, Casp A (1998) Quantification of significant volatile components of pacharán. Z Lebensm Unters Forsch A 206(6):414–416

    Article  Google Scholar 

  75. Soufleros EH, Natskoulis P, Mygdalia AS (2005) Discrimination and risk assessment due to the volatile compounds and the inorganic elements present in the Greek marc distillates Tsipouro and Tsikoudia. OENO One 39(1):31–45

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Food Engineering, Çukurova University, Sarıçam, Adana, Turkey

    Turgut Cabaroglu, Merve Darıcı & Abdullah Ozonur

Authors
  1. Turgut Cabaroglu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Merve Darıcı
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Abdullah Ozonur
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Turgut Cabaroglu .

Editor information

Editors and Affiliations

  1. Faculty of Pharmaceutical Sciences, University of Bordeaux, Bordeaux, France

    Jean-Michel Mérillon

  2. UMRt BioEcoAgro, University of Lille, Lille, France

    Céline Riviere

  3. UMRt BioEcoAgro, University of Lille, Lille, France

    Gabriel Lefèvre

Rights and permissions

Reprints and permissions

Copyright information

© 2023 Springer Nature Switzerland AG

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Cabaroglu, T., Darıcı, M., Ozonur, A. (2023). Aroma Composition of Aniseed and Aniseed-Flavored Beverages. In: Mérillon, JM., Riviere, C., Lefèvre, G. (eds) Natural Products in Beverages. Reference Series in Phytochemistry. Springer, Cham. https://doi.org/10.1007/978-3-031-04195-2_220-1

Download citation

  • DOI: https://doi.org/10.1007/978-3-031-04195-2_220-1

  • Received:

  • Accepted:

  • Published:

  • Publisher Name: Springer, Cham

  • Print ISBN: 978-3-031-04195-2

  • Online ISBN: 978-3-031-04195-2

  • eBook Packages: Springer Reference Chemistry and Mat. ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics

Publish with us

Policies and ethics

Search

Navigation