Details of Natural Product (NP)

General Information of Natural Product (ID: NP0454)
  Natural Product Name
Anethole
  Synonyms
ANETHOLE; trans-Anethole; 4180-23-8; 104-46-1; (E)-Anethole; p-Propenylanisole; 4-Propenylanisole; Anise camphor; Isoestragole; Monasirup; (E)-1-Methoxy-4-(prop-1-en-1-yl)benzene; Anethol; trans-Anethol; p-Anethole; Oil of aniseed; Anisole, p-propenyl-; trans-p-Propenylanisole; (E)-p-Propenylanisole; (E)-Anethol; Aniskampfer; Anethole, trans; 1-methoxy-4-[(E)-prop-1-enyl]benzene; p-1-Propenylanisole; (E)-1-(4-Methoxyphenyl)propene; 1-Methoxy-4-propenylbenzene; Nauli gum; 4-Methoxypropenylbenzene; trans-4-(1-Propenyl)anisole; cis-Anethol; trans-1-p-Anisylpropene; Anethole, trans-; Benzene, 1-methoxy-4-(1-propenyl)-; (E)-1-Methoxy-4-(1-propenyl)benzene; 1-Methoxy-4-(prop-1-en-1-yl)benzene; trans-p-Methoxy-beta-methylstyrene; 1-Methoxy-4-(1-propenyl)benzene; 4-Methoxy-1-propenylbenzene; p-Propenylphenyl methyl ether; FEMA No. 2086; 1-methoxy-4-[(1E)-prop-1-en-1-yl]benzene; Propene, 1-(p-methoxyphenyl)-; t-anethole; UNII-Q3JEK5DO4K; 1-Propene, 1-(4-methoxyphenyl)-; trans-1-Methoxy-4-(1-propenyl)benzene; trans-p-Anethole; Benzene, 1-methoxy-4-(1E)-1-propenyl-; NSC 4018; MFCD00009284; Q3JEK5DO4K; p-Methoxy-.beta.-methylstyrene; CHEBI:35616; NSC4018; Anethole (NF); Anethole [NF]; (E)-1-p-Methoxyphenylpropene; NSC-209529; DSSTox_CID_87; Methoxy-4-propenylbenzene; trans-1-(p-Methoxyphenyl)-1-propene; trans-1-(4-Methoxyphenyl)-1-propene; DSSTox_RID_75356; DSSTox_GSID_20087; 1-Methoxy-4-((1E)-1-propenyl)benzene; E-anethole; Benzene, 1-methoxy-4-(1E)-1-propen-1-yl-, homopolymer; trans-Anethole (natural); 1-(4-Methoxyphenyl)-1(3)-propene; Acintene O; Nauli ''gum''; (E)-1-methoxy-4-(prop-1-enyl)benzene; p-(1-Propenyl)anisole; 26795-32-4; 4-(1-propenyl)anisole; Propenylanisole, p-, (E)-; CAS-4180-23-8; Anethol (synthetic); Benzene, 1-methoxy-4-(1-propen-1-yl)-; Anisole, p-propenyl-, trans-; Anisole, p-propenyl-, (E)-; CCRIS 2481; Benzene, 1-methoxy-4-(1E)-1-propen-1-yl-; 1-(p-Methoxyphenyl)propene; 1-p-Methoxyphenylpropene, trans-; Caswell No. 051B; p-Propenylmethoxybenzene; FEMA Number 2086; SR-05000001866; 1-(methyloxy)-4-[(1E)-prop-1-en-1-yl]benzene; 4-06-00-03796 (Beilstein Handbook Reference); Benzene, 1-methoxy-4-(1-propenyl)-, (E)-; EINECS 224-052-0; Methoxy-beta-methylstyrene, trans-p-; CHEBI:2716; NSC 209529; p-Methoxy-beta-methylstyrene; BRN 0636190; trans-1-(p-Methoxyphenyl)propene; 1-Methoxy-4-(1-propenyl)benzene, (E)-; CCRIS 6211; 1-Methoxy-4-[1-propenyl]benzene #; Anisole, trans-; HSDB 1427; Synthetic Anethole; Nauli 'gum'; Anethole (natural); Benzene, 1-methoxy-4-(propenyl)-; EINECS 203-205-5; EINECS 256-753-2; (E)?-Anethole; EPA Pesticide Chemical Code 015604; BRN 0774229; trans-Anethole, 99%; trans-4-Propenylanisole; AI3-00380; 4-trans-propenyl-anisole; Spectrum5_000727; EC 224-052-0; ghl.PD_Mitscher_leg0.12; SCHEMBL48599; BSPBio_002818; trans-p-Methoxypropenylbenzene; 2-06-00-00523 (Beilstein Handbook Reference); SPECTRUM1503705; WLN: 2U1R DO1; Anethol, natural, 99%, FG; CHEMBL452630; DTXSID9020087; Trans-Anethole ((E)-Anethole); WLN: 2U1R DO1 -T; (E)-1-Methoxy-4-propenylbenzene; HMS1922I20; HMS2089P20; HMS2093I09; HMS3885E16; Pharmakon1600-01503705; ZINC967630; trans-Anethole, analytical standard; HY-B0900; NSC-4018; Tox21_202282; Tox21_300132; BBL027751; CCG-38720; NSC209529; NSC758626; s3779; STK801277; trans-p-Methoxy-.beta.-methylstyrene; trans-Anethole, >=99%, FCC, FG; AKOS000121299; DS-2756; NSC-758626; methyl 4-(prop-1-en-1-yl)phenyl ether; NCGC00091493-02; NCGC00091493-03; NCGC00091493-04; NCGC00091493-05; NCGC00091493-06; NCGC00091493-07; NCGC00254015-01; NCGC00259831-01; AC-34207; LS-13792; SBI-0052758.P002; trans-Anethole, purum, >=98.0% (GC); Benzene,1-Methoxy-4-(1-Propenyl)-,(E)-; P0494; S3990; X8716; Z4733; A14711; D02377; D70168; AB00053256-02; AB00053256_03; A873002; Q255564; Q-201853; SR-05000001866-1; SR-05000001866-2; W-108812; BRD-K49060658-001-01-5; trans-Anethole, primary pharmaceutical reference standard; UNII-A79C64YD3Q component RUVINXPYWBROJD-ONEGZZNKSA-N; Anethole, United States Pharmacopeia (USP) Reference Standard; BENZENE,1-METHOXY,4-PROPENYL(TRANS) TRANS ANETHOL; trans-Anethole, Pharmaceutical Secondary Standard; Certified Reference Material
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  Formula C10H12O
  Weight 148.2
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
  InChI Key RUVINXPYWBROJD-ONEGZZNKSA-N
  Isomeric SMILES C/C=C/C1=CC=C(C=C1)OC
  Canonical SMILES CC=CC1=CC=C(C=C1)OC
  External Links PubChem ID 637563
CAS ID 4180-23-8
NPASS ID NPC99886
HIT ID C0905
CHEMBL ID CHEMBL452630
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [1]
              Species Info Factor Info
               Experiment Detail
Populations of A. annua cultivar 'Jeevanraksha' and accession Suraksha were grown in the experimental field plot of the Institute at New Delhi. The seeds were sown in January 2004, seedlings transplanted in late February 2004 and aerial parts (flowers, leaves and stems from the upper 0.5 m of crop canopy) sampled in late October 2004.
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               Factor Function
Ninety-seven compounds comprising 91.3% of the total oil of 'Jeevanraksha' were identified. Forty-three monoterpenes (56.6%), 32 sesquiterpenes (31.1%), and 2 diterpenes (0.2%) comprised bulk of the oil (87.9%). The oil was devoid of artemisia ketone and contained camphor (13.5%), 1,8-cineole (9.4%), trans-sabinol (7.1%), p-mentha-1(7), 5-dien-2-ol (6.3%), myrcene (4.7%), germacrene D (4.4%), (E)-beta-farnesene (3.9%), beta-caryophyllene (3.7%), dihydroartemisinic lactone (3.0%) and p-cymene (2.0%) as the major constituents. Eighty-six compounds representing 93.3% of the composition were identified in the Suraksha oil. This oil contained artemisia ketone (47%), 1,8-cineole (8.4%), camphor (5.9%) and alpha-pinene (5.2%) as the major components.
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               Factor Part Location NP Content
 
Artemisia annua accessions Suraksha
 Aerial parts India
NP Content: <0.05 %
 
Artemisia annua cv. Jeevanraksha
 Aerial parts India
NP Content: <0.05 %
      Species Name: Coriandrum sativum
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
Two samples (20 kg each) of mature coriander (Coriandrum sativum L.) fruits were used for this study. The first was purchased from a spice market of Korba in Tunisia (Tn), the second, from Canada (Can), was supplied by General Herboristerie Laboratory (Marseille, France).
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               Factor Function
The first from Tunisia (Tn) and the second from Canada (Can). The highest essential oil yield was observed for Can with 0.44% (w/w) and 0.37% (w/w) for Tn. Forty-five compounds were identified in the essential oils and the main compound of both samples was linalool. The total phenol contents varied between two coriander fruit samples; Can sample presented high polyphenol contents (15.16 mg GAE/g) compared with Tn one (12.10 mg GAE/g). Significant differences were also found in total tannin contents among representing 0.7 mg GAE/g in Can and 0.34 mg GAE/g in Tn. The highest contents of total flavonoids were observed in Can sample with 13.2 mg CE/g.
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               Factor Part Location NP Content
 
Locality: Canada
 Fruits Canada
NP Content: 0.1 %
 
Locality: Korba, Tunisia
 Fruits Tunisia
NP Content: 0.1 %
      Species Name: Tagetes patula
  Factor Name: Month Variation; Nitrogen Treatment; Phosphorus Treatment; Potassium Treatment [3]
              Species Info Factor Info
               Experiment Detail
The plants were cultivated in the Botanical Garden of the University of Agriculture, Plovdiv/Bulgaria on meadow-carbonate soil with neutral reaction (pH 7.1-7.2) and were harvested during the flowering period (July and September). The reserves of nitrogen, phosphorus and potassium in the soil (NPK) were: NH4+ 31.42 mg/kg; NO3- 16.66 mg/kg; P2O5 12.3 mg/100 g and K2O 11.4 mg/100 g. Ammonium nitrogen and nitrate nitrogen were extracted from the soil with a 1% solution of KCI and were determined by consecutive distillation on a Parnas-Vagner apparatus. Phosphorus was determined by the Egner-Ream method and potassium was extracted with 2 n HCI and was determined by flame photometry. The plants were grown as seedlings and were planted in a two-row bed 50 × (20 + 20) cm in patches of 5 m2. A scheme on the increase was used for the introduction of N, P and K fertilizers. The experiment was carried out as a randomized block modus - 15 variants in 4 replications (6 levels for N and 4 levels for P and K). Phosphorus (triple superphosphate - 50 % active substance) and potassium (potassium sulphate - 50 % active substance) were introduced only once before planting. Nitrogen (the ammonium nitrate - 33 % active substance) was introduced in three portions - during preparing of the soil, during the plants drafting (active vegetation) and at the full bloom.
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               Factor Function
The highest oil yield was obtained from leaves in July for N4P2K4 (0.63%) and the basic components were piperitenone (29.4%) and piperitone (13.5%). The mineral fertilization had no effect on the oil yield from the flowers. Regardless of the variant, it was found that the flower oils in July were rich in caryophyllene oxide (12.0-48.4%) and piperitenone (3.0-7.0%), while the oil composition in September was different.
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               Factor Part Location NP Content
 
Flower: (Harvesting time: July) + (Level of fertilization: N0P0K0)
 Flowers Plovdiv, Bulgaria
NP Content: 0.3 %
 
Flower: (Harvesting time: September) + (Level of fertilization: N2P4K4)
 Flowers Plovdiv, Bulgaria
NP Content: 0.3 %
 
Flower: (Harvesting time: September) + (Level of fertilization: N4P2K4)
 Flowers Plovdiv, Bulgaria
NP Content: 0.3 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N4P2K4)
 Leaves Plovdiv, Bulgaria
NP Content: 0.3 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N4P4K2)
 Leaves Plovdiv, Bulgaria
NP Content: 0.2 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N0P0K0)
 Leaves Plovdiv, Bulgaria
NP Content: 1.3 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N2P4K4)
 Leaves Plovdiv, Bulgaria
NP Content: 0.1 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N4P2K4)
 Leaves Plovdiv, Bulgaria
NP Content: 0.1 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N4P4K2)
 Leaves Plovdiv, Bulgaria
NP Content: 0.1 %
      Species Name: Tanacetum larvatum
  Factor Name: Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
Aerial parts of T. larvatum were collected in July and August during a five-year period, starting in 2001, in Montenegro on several locations: Planinica (Sample a), Visitor (Sample b) and Sinjajevina (Sample c).
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               Factor Function
Sixty-four components were identified, representing 83.1%, 96.6% and 89.4% of the total oils content in the Planinica [Sample a], Visitor [Sample b] and Sinjajevina [Sample c], respectively. The major constituent in Samples a and b , was oxygenated monoterpene, trans-sabinyl acetate (38.1% and 55.8% respectively). Monoterpene hydrocarbons, beta-pinene (13.5%) and santolinatriene (30.6%), were found to be the dominant components in Sample c. The toxic trans-sabinyl acetate was present only in traces in this sample. trans-Chrysanthenyl acetate, as one of major components in feverfew essential oil, has not been previously identified in the investigated essential oils.
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               Factor Part Location NP Content
 
Locality: Sinjajevina, Montenegro
 Aerial parts Montenegro
NP Content: 0.3 %
 
Locality: Visitor, Montenegro
 Aerial parts Montenegro
NP Content: 0.4 %
References
1 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
2 Chemical Composition and Antioxidant Activities of Tunisian and Canadian Coriander (Coriandrum sativum L.) Fruit
3 Effect of Mineral Fertilization on the Essential Oil Composition of Tagetes patula L. from Bulgaria
4 Intraspecific Variation of Tanacetum larvatum Essential Oil