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Aniseed - Chemical structure, Production, Main uses in food processing

nutrition

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Aniseed




M. O¨ zgu¨ ven, University of Cukurova, Adana

1     Introduction Source:  Pimpinella  anisum  L.  (Syn.  Anisum  vulgare  Gaertn.;  Anisum  officinarum Mo¨ nch; Apium anisum (L.) Crantz; Carum anisum (L.) Baill.; Selinum anisum (L.) E.H.L. Krause;  Pimpinella  anisum  (var.)  cultum  Alef;  Sison  anisum  Spreng.;  Tragium  anisum Link).1,2

Family: Apiaceae (= Umbelliferae) Synonyms: Aniseed, Anis seed, Anis, Anise, Sweet cumin Parts used: Seeds (fruits), oil

Classification:

Division:                         Spermatophyta Subdivision:          Angiospermae Class:                              Magnoliospida Subclass:    Rosidae

Order:                             Apiales Family:      Apiaceae Genus:                                        Pimpinella3

Anise  is  an  annual  plant  that  reaches  an  average  height  of  30–50 cm.  The  plant  is completely covered with fine hairs. The root is thin and spindle-shaped, the stem up, stalk- round,  grooved  and  branched  upward  (see  Fig.  1).  In  midsummer  the  thin  stems  are topped with umbrella-shaped clusters of tiny white flowers, which are heavy enough to make the stems flop. They turn into seedlike fruits. Anise is a cross-pollinating species and is  genetically  heterogeneous.  The  fruit  is  an  ovoid-pearshaped  schizokarp  somewhat compressed at the  side. The two-part  fruits separate  heavily. The  carpophore is almost two-piece up to the base. Commercially available aniseed usually contains the whole fruits and occasionally parts of the fruitstalk (see Fig. 2). The fruits with the style-foot are 3–

5 mm  long,  1.5–2.5 mm  wide  and  2–4 mm  thick.  Vittae  (oil  ducts)  are  almost  always present embedded in the fruit wall on the dorsal surface, sometimes in or directly beneath the ridges. The fruits are downy. Their colour is greyish-green to greyish-brown.4,5


Fig. 1    Pimpinella anisum L.

2     Chemical structure

Anise contains:

   1–4% volatile oil;

   coumarins: bergapten, umbelliprenine, umbelliferone, scopoletin;

   ca.  8–16%  lipids,  including  fatty  acids:  50–70%  petroselinic  acid  (C18:1),  22–28% oleic acid (C18:1), 5–9% linoleic acid (C18:2) and 5–10% saturated fatty acids mostly palmitic acid (C16:0);

   -amyrin, and stigmasterol and its salts (palmitate and stearate);

   flavonoid glycosides: quercetin-3-glucuronide, rutin, luteolin-7-glucoside, isoorientin, isovitexin, apigenin-7-glucoside (apigetrin) etc;

   myristicin;

   ca. 18% protein;

   ca. 50% carbohydrate and others.

Fatty acids can be obtained by extraction, as in the case of caraway, in the remainders of   oil   extraction   via   steam   distillation.   Lauric   acid,   which   is   most   important   to


Fig. 2    Dried aniseed.

oleochemistry, is obtained from petroselinic acid which is found in high quantities (50–

70%) in anise. Fatty oil shows excellent future potential. Successful production of anise seed  for  economical  oil  production  would  probably  occur  if  the  seed  yields  could  be improved significantly,  and  high content  of oil  and essential  oils and  large  quantity  of petroselinic acids could be reached.6,7

The major constituent in volatile oil of aniseed is trans (E)-anethole (75–90%7; 80–

90%8;  86%9;  96–98%10;  86–89%11;  89–92%12).  Methylchavicol  (estragole)  (4.95%9;

1.73.7%10;   3.6–5%11;   1.0–2.4%12),   anise   ketone   (para-methoxyphenylacetone)

(0.78%9;  0.5–0.9%11)  and    -caryophyllene  are  also  present,  but  in  lesser  relative amounts.  Other  components  in  minor  concentrations  include  anisaldehyde,  anisic  acid

(oxidation  products  of  anethole),  linalool,  limonene,         -pinene,  acetaldehyde,  p-cresol, creosol, hydroquinine,                                 -farnasene,    -himachalene and ar-curcumene.7

3     Production

3.1     Cultivation

Anise is cultivated in Turkey, Egypt, Spain, Russia, Italy, India, Greece, Northern Africa, Argentina, Malta, Romania and Syria. Anise is primarily exported from Turkey, and also from Egypt and Spain in particular. From an industrial standpoint, the quality differences between anise seed from different origins are not significant and therefore specifications need not limit the spice to a specific country of origin.13,14,15

P. anisum requires a warm and long frost-free growing season of 120 days. The plant needs  a  hot  summer  to  thrive  and  for  seeds  to  ripen.  The  reported  life  zone  for  anise production is 8 to 23sC with 0.4 to 1.7 metres of precipitation on a soil pH of 6.3 to 7.3. Anise develops best in deep, rich, well-drained, sandy and calcerous soils. Cold, loamy


and  moist  soils  are  unsuitable  for  the  cultivation  of  anise.  During  germination  anise tolerates  salinity  up  to  160   m  NaCl.  The  thousand  seeds  weight  of  the  part-fruits amounts  to  1.5  to  3.0 g  and  should  have  a  minimum  purity  of  90%  and  a  minimum germination of 70%.

Ripe-fruits seeds germinate relatively quickly. The germination time is 14 days. Only seeds  from  the  previous  years  harvest  germinate  well.  Long  storage  quickly  reduces germination vigour: seeds stored for five years will no longer germinate. Planting begins when the soil in the beds is warmed. Optimum soil temperature for germination is 18–

21sC. It is essential to prepare good seedbeds and to create a good contact between the planted  seed  and  the  soil  because  the  seeds  are  small  and  have  low  germination percentage (70%). The planting is carried out in spring or autumn depending on the areas it is cultivated. The seeds with a seeding rate of 20–25 kg/ha are sown in rows 20–30 cm apart,  at  a  depth  of  1 cm.  The  plant  develops  slowly  after  germination  and  for  the following few weeks it is necessary to control weeds closely. It is recommended to apply fertilizers at a rate of 80–100  kg K2O and 50–75 kg P2O5  per hectare. With nitrogen, it is important   to   be   careful,   since   excessive   nitrogen  fertilization   results   in   luxuriant vegetative growth with reduced yields, and increased vulnerability to lodging. 50–100 kg/ ha  N  is  normally  enough.  The  small  white  flowers  bloom  in  midsummer,  and  seed maturity  usually  occurs  one  month  after  pollination,  when  the  oil  content  in  the  dried fruits  is  about  2.5%.  Anise  seeds  are  harvested  between  from  the  end  of  July  to  the beginning of September, depending on the cultivation areas. Yields of seed up to 500–

1000 kg/ha  have  been  achieved.  P.  anisum  is  recommended  in  companion  planting  to repel   aphids   and   cabbage   worms.   The   flowers   attract   parasitic   wasps.5,6,16,17,18

Constituents  in  plant  volatile  oils  are  known  to  be  useful  in  pest  control.  Various authors have reported that vapours of essential oils extracted from anise were found to be toxic  to  two  greenhouse  pests,  viz.  the  carmine  spider  mite,  Tetranychus  cinnabarinus and cotton aphid, Aphis gossypii Glov.19  Sarac and Tunc20  indicated that the essential oil of anise had a high residual toxicity to adults of Tribolium confusum, and was the most repellent to Sitophilus oryzae adults in food preference tests.

3.2     The production of anise oil

The world production of anise oil amounts to 40–50 tons per annum. The most significant importing countries of anise oil are the USA and France. Russia, Spain and Poland are among  the  largest  producers  of  anise  oil.  There  is  no  distillation  of  anise  oil  and  no production of anethole in many of the countries which cultivate the crop.21,22,23

Anise oil is steam distilled from the crushed seeds of the plant Pimpinella anisum. The process of steam  distillation  is the  most widely  accepted  process for the  production  of essential  oils  on  a  large  scale.  A  still  is  charged  with  plant  material  to  be  processed. Steam is introduced at the base of the still and the crushed anise seeds volatile elements evaporate  with  the  steam.  A  condensation  process  turns  this  vapour-mix  into  a  liquid form  of  water  and  essential  oil.  The  essential  oil  floats  on  top  of  the  water  and  is separated  off.  The  essential  oil  of  aniseed  is  a  colourless  to  faintly  yellow  oil  which solidifies upon cooling to about 15–19sC due to the crystallization of anethole.

Oleoresin  anise  is  a  yellowish-green  to  orange-brown  fluid  oleoresin.  Volatile  oil content of oleoresin anise is 15–18%. The presence of a large quantity of fixed oil in this product limits its shelf-life and the addition of a permitted antioxidant is advised.24  Anise and anise oil are widely used as flavouring ingredients in all major categories of foods, including  alcoholic  and  non-alcoholic  beverages,  frozen  dairy  desserts,  sweets,  baked


goods,  gelatines  and  puddings,  and  meat  and  meat  products.  The  highest  average maximum use levels for anise oil are about 0.06% (570 ppm) in alcoholic beverages and

0.07%  (681 ppm)  in  sweets.7   Suggested  use  rate  of  oleoresin  anise  is  7.5  to  9%.24   In Turkey the different types of aniseed spirits are distinguished by their anise seed content: Yeni  raki  (80 g/L  aniseed),  Kulup  raki  (100 g/L  aniseed)  and  Altinbas  raki  (120 g/L aniseed).25

3.3     Stability during storage, irradiation and heat processing

Anise  has  to  be  stored  away  from  daylight  and  kept  in  a  dry  place  in  cool  conditions

(DAB 10 Eur, O¨ AB 90, Helv VII). The average loss of the content of the volatile oil has been calculated at 1% of the original content per month. The content of trans-anethole decreases from 89% to 73% during a storage of six weeks with the influence of sunlight, while  the  content  of  cis-anethole  increases  from  0.8  to  4.5%  and  the  content  of anisaldehyde from 0.8 to 7.0%. At the same time additional decomposition products are formed.  Investigations  on  airsealed,  grinded  aniseed  clearly  show  changes  of  odour within  the  first  12  months  if  the  temperature  of  storage  exceeds  5sC.  Because  of  the sensitivity to light and oxidation it is recommended that the volatile oil of anise is stored in well filled and well closed containers (glass or tin, but not plastic) protected against daylight  (DAB  10,  BP  88,  PFX,  O¨ AB  90,  HELV  VII).  Moreover,  PFX  demands  a storage temperature below 10sC and BP 88 a storage temperature below 25sC. With the influence  of  daylight,  trans-anethole  is  transformed  into  its  more  toxic  isomer  cis- anethole.26



It is reported that there is an increase in anise ketone, anisaldehyde and anisic acid9 and decrease in trans-anethole27  of anise oil during long-term storage. Moisture content of the seeds or humidity of the storage atmosphere is the most important parameter to be considered  in  preserving  the  desired  properties  of  anise.  At  high  moisture  levels deteriorative reactions and off-flavours are inevitable in addition to the increased rate of loss  of  volatile  oil  by  diffusion.  Oxidation  reactions  are  responsible  for  the  loss  of  oil during  storage  by  converting  the  components  mostly  to  acids  and  aldehydes.  Also, daylight  catalyzes  oxidative  reactions  and  increases  the  rate  of  deterioration.  Extreme variations in the moisture content of the storage atmosphere favour oil evaporation and particularly   oxidation.28    The   dimers   of   anethole   (dianethole)   and   anisaldehyde

(dianisoin)   are   mentioned   repeatedly   in   the   literature14,29,30    and   are   supposedly responsible  for  the  oestrogenic  activity  in  old  drugs  and  in  stored  oils  under  exposure to sunlight, and air could not be found after thorough investigation.31

One interesting item to note in this spice is that when the ground product is irradiated, a  slightly  putrid  off  odour  and  flavour  results.  This  contradicts  most  research  that irradiation does not change the chemical properties of a spice when treated. It is possible that  it  does,  in  limited  cases,  change  the  flavour  balance  of  essential  oils.15  Similarly numerous authors report that volatile oil of anise, extracted after irradiation with 1.5 and

10 kGy -rays,  contained  the  most  oxygenated  compounds,  and  irradiation  caused  a general increase in oxygenated compounds at 1 kGy.32  Farag-Zaied et al.33  indicated that

-irradiation was effective in decontamination, especially at 10 kGy, but caused losses in the major components of flavour such as anethole, methylchavicol and anisealdehyde in anise.

Thermal treatment at 70sC for 15 minutes reduced the microbial count and pathogenic microbes, improving the anethole in anise, and washing the spice removed some of the microbes but improved markedly the anise flavour. Thermal and washing treatments may


be of value as simple natural techniques to produce spices with a good flavour and with an acceptable level of contamination.

Bendini et al.34  detected linear, unsaturated hydrocarbons in aniseed samples treated with          -rays  or  microwaves.  The  microwave  treatment  of  aniseeds  did  not  modify  the hydrocarbon profile with respect to the untreated samples. In contrast,   -irradiation gave rise  to  a  series  of  unsaturated  hydrocarbons  of  which  C16:2,  C16:1,  C17:2  and  C17:1 were  determined.  In  most  cases,  when  these  products  were  quantified,  their  amounts increased with the dose of radiation. C17:1 could be considered as the marker of the    - irradiation   treatment.   The   essential   oil   of   anise   extracted   from                         -irradiated   and microwaved fruits exhibit antioxidant properties.   -irradiation and microwave treatments have no effect on the antioxidant properties of essential oil. Essential oil extracted from the                                                 -irradiated  fruits  are  more  effective  as  antioxidants  than  those  produced  from microwaved fruits.35,36

4     Main uses in food processing

Aniseed’s   long   popularity   throughout   so   many   lands   stems   from   its   many   uses: flavourant,  culinary,  household,  cosmetic  and  medicinal.  While  the  entire  plant  is fragrant, it is the fruit of anise, commercially called aniseed, that has been highly valued since antiquity.  Aniseed is one  of the  oldest spices  used widely  for flavouring  curries, breads, soups, baked goods such as German springerle, and Italian biscotti, sweets (e.g. licorice  candies,  especially  aniseed-balls),  dried  figs,  desserts,  cream  cheese,  pickles, coleslaw,  egg  dishes,  non-alcoholic  beverage.  It  is  a  favourite  flavouring  for  alcoholic drinks in the Mediterranean region, such as French Pastis, Pernod, Anisette, and Ricard, Greek  Ouzo,  Turkish  Raki  and  Arabian  Arak,  and  also  South  American  Aguardiente, Russian  Allasch,  Puerto  Rican  Tres  Castillos.  Aniseed  oil  is  a  component  in  German Boonekamp,   Benediktener,   Goldwasser   and   Spanish   Pacharan   and   Ojen.   Anisette combines anise, coriander and fennel seeds in sweet vodka. Anise and anise oils are used in Italian sausage, pepperoni, pizza topping and other processed meat items. Anise is an essential component of Italian anise cake and cookies. All parts of the plant can be used in the kitchen. The flowers and the leaves can be added to fruit salads. Freshly-chopped leaves also enhance dips, cheese spreads, vegetables, or green salads. Mixed into stews and soups, the stem and roots of anise give just a hint of licorice.6,15,16,18,26

The essential oil is valuable in perfumery, in dentrifices as an antiseptic, toothpaste, mouthwashes, soaps, detergents, lotions and skin creams, in tobacco manufacture, with maximum use levels of 0.25% oil in perfumes. It is also used to mask undesirable odours in drug and cosmetic products. The oil is used for production of anethole and sometimes as sensitizer for bleaching colours in photography.7,16,23

5     Functional properties

The  pharmaceutical  data  mentioned  in  the  literature  mainly  refer  to  anise  oil  and anethole. Anethole is structurally related to the catecholamines adrenaline, noradrenaline and dopamine.37  Anise oil and anethole have a number of functional properties:

   antibacterial

   antifungal


   antioxidant

   stimulant, carminative and expectorant.

The antibacterial activities of the essential oil distilled from Pimpinella anisum against Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Corynebacterium ovis were evaluated.  Against S. pyogenes, aniseed oil was equally effective  in the pure state and at dilution up to 1:1000. Against C. ovis, aniseed oil was equally effective at dilutions up to 1:100 and at higher dilutions.38  The inhibitory properties of anise essential oil, alone or in combination with either benzoic acid or methyl-paraben, against Listeria monocytogenes   and   Salmonella   enteriditis   were   investigated.   S.   enteriditis   was particularly  sensitive  to  inhibition  by  combinations  of  anise  essential  oil  with  methyl- paraben.  L.  monocytogenes  was  less  sensitive  but  exhibited  significant  reductions  in growth in response to combinations of essential oil with methyl-paraben.39

Kubo40  reported that anethole, a naturally occurring phenylpropanoid extracted from aniseed,  exhibited  a  broad  antimicrobial  spectrum  and  the  antifungal  activity  (against Candida   albicans)   of   two   sesquiterpene   dialdehydes,   polygodial   and   warburganal

(extracted from Polygonum hydropiper), was increased 32 fold when combined with low concentrations  of  anethole.  In  a  study  of  the  volatile  oil  from  aniseed,  significant antifungal activity against members of the genera Alternaria, Aspergillus, Cladosporium, Fusarium  and   Penicillium  was  recorded  at  concentrations   of  500 ppm,  the  active constituent  having  been  identified  as  anethole.41    Anethole  also  inhibits  growth  of mycotoxin  producing  Aspergillus  species  in  culture.  Anethole  has  been  reported  to  be mutagenic in Ames Salmonella  reversion  assay. Anethole,  anisaldehyde  and myristicin

(in aniseed), along with d-carvone (present in P. anisum plant), have been found to have mild insecticidal properties.7  Pharmacological studies were carried out in rats and mice, and  anise  oil  showed  significant  antipyretic  activities  in  rats.42   Curtis43   reports  that synthetic  versions  of  compounds  in  herbs  and  spices  such  as  trans-anethole  have inhibitory and lethal activity against food spoilage yeast Debaromyces hansenii.

There is some evidence of anise oil’s effectiveness as an antioxidant. Gurdip et al.44 investigated  the  antioxidant  activity  of  essential  oil  from  spice  materials  on  stored sunflower oil and found that anise oil possessed excellent antioxidant effects, better than those of synthetic antioxidant, butylated hydroxytoluene.

Anise oil is reported to be carminative and expectorant. The reputed lactogogic action of anise has been attributed to anethole, which exerts a competitive antagonism at dopamine receptor  sites  (dopamine  inhibits  prolactin  secretion),  and  to  the  action  of  polymerized anethole,   which   is   structurally   related   to   the   oestrogenic   compounds   stilbene   and stilboestrol. Anethole is also structurally related to the hallucinogenic compound myristicin. Bergapten,  in  combination  with  ultraviolet  light,  has  been  used  in  the  treatment  of psoriasis.37 Anise oil is used as carminative, stimulant, mild spasmolytic, weak antibacterial, and expectorant in cough mixtures and lozenges, among other preparations. It can be used internally  for  dyspeptic  complaints  and  externally  as  an  inhalant  for  congestion  of  the respiratory tract. The whole, crushed, or ground crude drug can be used for infusion, and other galenical preparations; e.g. several instant teas as powders containing aqueous extracts of aniseed, or as tea paste, some preparations with micro-encapsulated anise oil. Anise seed and anise oil are subjects of German official monographs; 3.0 g of seed or 0.3 g of essential oil  (mean  daily  dose)  allowed  as  a  bronchial  expectorant  for  upper  respiratory  tract congestion and as gastrointestinal spasmolytic.7,31

Anise  may  have  other  potential  health  benefits.  The  effect  of  the  beverage  extracts anise  on  absorption  of  iron  was  tested  in  tied-off  intestinal  segments  of  rats.  Results


showed that the beverage of anise promoted Fe absorption.45  Preparations containing 5–

10% essential oil are used externally.7,31  The oil added to an ointment helps in cases of aches   of   muscles   and   neuralgia.6    Olfactory   masking   with   aniseed   oil   decreased aggression  and  prevented  the  decrease  in  milk  production  in  dairy  cattles.46    It  is reported that anethole stimulates hepatic regeneration in rats, and also shows spasmolytic activity.  Chemically  it  is  used  as  a  precursor  in  the  manufacture  of  anisaldehyde. Occurring  in  the  essential  oil  of  P.  anisum,  p-anisaldehyde  has  fungistatic  activity;  p- cresol  is  a  disinfectant  agent  and  cresols  are  used  in  veterinary  practice  as  local antiseptics,  parasiticides  and  disinfectants;  hydroquinone  has  antibacterial,  antitumour, antimitotic and hypertensive activities. It is cytotoxic to rat hepatoma cells. Uses include a depigmentor, an antioxidant and a photographic reducer and developer.47



In traditional medicine anise is reportedly used as aromatic carminative, stimulant and expectorant; also as oestrogenic agents to increase milk secretion, promote menstruation, facilitate birth, increase libido, and alleviate symptoms of male climacteric.7  Aniseed is traditionally regarded as an aphrodisiac. Externally, the oil may be used as an ointment base for the treatment of scabies. The oil by itself will help in the control of lice and as a chest rub for bronchial complaints. The oil is often mixed with oil of Sassafras albidum for skin parasites and with that of Eucalyptus globulus as a chest rub.18

6     Toxicity and allergy

Aniseed contains anethole and estragole which are structurally related to safrole, a known hepatotoxin and carcinogen. Although both anethole and estragole have been shown to cause hepatotoxicity in rodents, aniseed is not thought to represent a risk to human health when it is consumed in amounts normally encountered in foods.37  Anise and oil of anise are generally regarded as safe for human consumption.

The  toxicity  and  cancerogenity  of  anethole  are  controversial.  Anethole  has  two isomers (trans and cis), the cis (Z) isomer being 15–38 times more toxic to animals than the trans (E) isomer.7  The major component of the natural volatile oil of anise (80–96%) is   trans-anethole,   which   is   most   likely   non-cancerogenic.   Trans-anethole   will   be accompanied by cis-anethole (maximum 0.3–0.4%), which is not caused by distillation, but exists naturally in anise seeds. In case of storage without protection of daylight the forming of cis-anethole is possible. Synthetic trans-anethole contains higher quantities of toxic cis-anethole compared to natural trans-anethole and therefore it is not used in food processing. Cases of intoxication with the volatile oil of anise are not known.26  Current United States Pharmacopeia (USP) and Food Chemical Codex (FCC) specifications for anethole do not require differentiation between the isomers.7

Aniseed may cause an allergic reaction. It is recommended that the use of aniseed oil should  be  avoided  in  dermatitis,  or  any  inflammatory  or  allergic  skin  conditions.37

Patients  with  an  allergy  to  pollen  are  often  suffering  from  ‘spice-allergy like  celery, carrot, etc. Skin-prick tests with anise extracts in several cases result in positive allergic reactions.26   Freeman48   reports  an  atopic  man  who  experienced  cutaneous  allergy  and periorbital  edema  after  preparing  and  eating  fresh  dill.  The  patient  reported  here demonstrated reactive skin tests and positive radio allergo sorbent test (RAST) to other members of the Umbelliferae including aniseed in addition to dill. Similarly Fraj et al.49 describe a case of occupational asthma induced from aniseed dust sensitization. A skin- prick test carried out with 13 spices showed positive reactions only to aniseed extract. When  consumed  in  sufficient  quantities,  anise  oil  may  induce  nausea,  vomiting,


seizures  and  pulmonary  edema.  Contact  of  the  concentrated  oil  with  skin  can  cause irritations.16  Anethole has been reported to be the cause of dermatitis (erythema, scaling and vesiculation) in some people.7  Compared with star anise however, the sensitization effect of anise oil is lower.26

7     Quality and regulatory issues The recommended moisture limits from the American Spice Trade Association (ASTA) is 10% in whole and in ground anise. Ash and acid insoluble ash should be no greater than 6.0% and 1.0%, respectively.15  According to BHP 1983:31  foreign organic matter, not  more  than  2%;  other  fruits and  seeds, not  more  than  2%;  total  ash,  not  more  than

10%;  acid-insoluble  ash,  not  more  than  2.5%.  The  minimum  content  of  volatile  oil  of anise is 2% (BHP 1983; Ph. Eur, 2).31  Anise oil is a colourless to pale yellow, strongly refractive liquid, having the characteristic odour and taste of anise. It should contain 84–

93% trans-anethole (major component and typical carrier of odour and flavour) and 0.5–

6.0%  methylchavicol  (=estragole,  which  smells  like  anise  but  does  not  have  its  sweet taste) (HPLC profile Ph. Eur.).14

Anise oil is frequently adulterated with the lower priced star anise oil, which, according to several Pharmacopoeiae, is also considered ‘anise oil’. Star anise (Illicium verum Hook f.) is the dried fruit of a tall evergreen tree, which is native to southern China and northern Vietnam. The profile of star anise oil is similar to that the Pimpinella oil and the two are equally acceptable and interchangeable in use. But, strictly from the flavouring viewpoint, anise oil (P. anisum) is undoubtedly superior to star anise oil (I. verum), the latter having a somewhat harsher odour. Pharmacopoeiae therefore demand the specification of the plant of origin out of which the anise oil was extracted (whether from aniseed, P. anisum or star anise, I. verum, which can be determined). This is obviously for the sake of consumer protection, since star anise oil is substantially cheaper than the oil extracted from anise. Characteristic of genuine aniseed oil is the presence of up to 5% of the 2-methylbutyryl ester of 4-methoxy-2-(1-propenyl)-phenol (= pseudoisoeugenyl 2-methylbutyrate). On the other  hand,  fruit  oil  of  I.  verum  is  characterized  by  the  presence  of  Foeniculin.  The provenance of an oil can be determined by detection of each of these two substances. Star anise oil further differs from P. anisum oil by its content of several terpene hydrocarbons

(THC) as well as its content of 1,4-cineol. This may explain why star anise oil does not reach the flavour quality of aniseed oil.14,26,31,50  Other adulterants are synthetic anethole and fennel oil. The latter can be detected by a change in the optical rotation. Much cheaper synthetic anetholes are also available but some carry a risk of toxicity, which precludes their use in food and drinks.50,51  A further criterion of quality is its solidification point which sinks with decreasing content of anethol. The solidification point of officinal anise oil lies between +15sC and +19sC (Ph. Eur.). Pure anethole becomes fluid above +23sC and solidifies at +21sC. All Pharmacopoeiae recommend checking physical properties like specific gravity, refractive index, optical rotation and temperature of solidification in order to get hints about the purity of anise oil. Table 1 lists physical properties according to different  sources. The  specifications  of the  limits  as mentioned  in the  Pharmacopoeiae vary slightly. Anise oil has to be dissolvable in 1.5 to 3.0 times its volume of EtOH 90%

(DAB 10, NFXVII, O¨ AB 90, Helv VII). This test is useful to exclude adulterations by fats, oils and mineral oils.26

Italian  anis  may  be  confused  (in  former  times  more  often,  nowadays  very  rarely)

occasionally  with  poisonous  fruits  of  Conicum  maculatum  L.  (hemlock).  Morpho-


Table 1    Physical properties of anise volatile oil according to different sources

Properties                 Turkish    Food        Pharmacopoeiae26         ISO53

anise11   chemical52

volatile    codex

oil        specification

Specific gravity (20sC)        0,990           0,978–0,988            0,979–0,994 (DAB10)          0.980–0990

Refractive index (20sC)    1,558             1,553–1,560            1,553–1,561 (DAB10)          1.552–1.559

Solidification point  19sC    > 15sC         > 15sC (BP 88)        + 15sC to + 19.5

Optical rotation (20sC)                            2s to + 1s                 2s to + 1s (BP 88)   2s to + 5s

logically, hemlock fruit can be recognized by the undulate (especially in the upper part of the fruit) ridges. Crushed fruits that are moistened with a potassium hydroxide solution should not smell like mouse urine (coniine). Adulteration with parsley or dill fruits can be detected readily by their smaller size and missing hairs. Nearly all anise fruits currently traded  are  impurified  with  up  to  1%  coriander  fruits.14,31   Adulteration  of  powdered aniseed or anise oil can be rapidly and reliably determined by direct mass spectroscopy via  the  marker compound  pseudoisoeugenyl  2-methyl-butyrate  which  only  occurs  in genuine ‘anise oil’; as little as 0.2–1.4% can be detected in the presence of 94% anethole, without the necessity of its having to be separated or the sample specially prepared.31

In  the  USA,  aniseed  is  listed  as  GRAS  (Generally  Regarded  As  Safe;  §182.10  and

§182.20). Aniseed is used extensively as a spice and is listed by the Council of Europe as a natural source of food flavouring (category N2). Anise seed and anise oil are subject to different pharmacopoeial Monographs: Aust., Br., Cz., Egypt., Eur., Fr., Ger., Gr., Hung., It., Neth., Rom., Rus., and Swiss.37  Aniseed is covered by the following: Anise DAB 10

(Eur), O¨ AB90, Helv VII, Pimpinella  BHP83, Aniseed Mar29. Anise oil is covered  by: DAB  10,  BP88,  NFXVI,  Essentia  anisi  Hisp  IX,  Huile  essentielle  d’anis  PFX,  Anisi aetheroleum   O¨ AB90,   Helv   VII,   Anise   Oil   BPC79,   Mar   29   (All   pharmacopoeias mentioned under Monographs except Hisp IX additionally allow Illicium verum Hook as plant of origin). Homeopathic guidance includes: Pimpinella anisum, ethanol. Decoctum hom. HAB1, Anisum hom. HAB 34, Anisum hom. HPUS88.26

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