General Information of Natural Product (ID: NP0456)
  Natural Product Name
(E)-Tagetenone
  Synonyms
trans-Ocimenone; (E)-Tagetenone; trans-Tagetenone; (e)-ocimenone; SCHEMBL2133996; (E)-Ocimenone (trans-ocimenone); (E)-2,6-Dimethylocta-2,5,7-trien-4-one; Q67879844
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  Formula C10H14O
  Weight 150.22
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H14O/c1-5-9(4)7-10(11)6-8(2)3/h5-7H,1H2,2-4H3/b9-7+
  InChI Key XUINKEIPBTYUJP-VQHVLOKHSA-N
  Isomeric SMILES CC(=CC(=O)/C=C(\\C)/C=C)C
  Canonical SMILES CC(=CC(=O)C=C(C)C=C)C
  External Links PubChem ID 6428431
CAS ID 33746-72-4

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Juniperus thurifera
  Factor Name: Altitude Variation; High Temperature Treatment [1]
              Species Info Factor Info
               Experiment Detail
The plant materials were collected for P1: 2900 m, Ait Akak, Oukaimden, Atlas Mts, Morocco, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 12/12/2003; P2, 2200 m, Plateau of Matat, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 18/03/2003; P3: 2000 m, Foret Islane, Oukaimden, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns,12/12/2003. A portion of the leaves from each of the three trees (per population) were air dried for 16 days at room temperature (ca. 22 &#8451) to produce the dried leaf samples.
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               Factor Function
The oil yields from fresh leaves showed on differences among geographical sources. Air dried leaves appeared to yield more oil at the highest elevation (1.03%, Ait Lkak, 2900 m) than lower sites (0.67%, Plateau of Matat, 2200 m; 0.57%, Foret Islane, 2000 m). The essential oils from each geographic site had very similar composition in fresh versus air dried leaves. The essential oils from provenance Ait Lkak and Plateau of Matat were very similar and characterized by a high sabinene content (21.2, 35.9%), in contrast to 10.% sabinene from the provenance Foret Islane. The oil from Foret Islane had a high delta-cadinene content with 12.7%, whereas Aik Akak and Plateau of Matat contained only 0.6 and 0.8%.
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               Factor Part Location NP Content
 
Fresh leaf: (Locality: Plateau of Matat, Tensift Al Haouz-Marrakech, Morocco; Altitude 2200 m)
Fresh leaves Plateau of Matat, Tensift Al Haouz - Marrakech, Morocco
NP Content: 0.3 %
 
Dry leaf: (Locality: Plateau of Matat, Tensift Al Haouz-Marrakech, Morocco; Altitude 2200 m)
Dry leaves Plateau of Matat, Tensift Al Haouz - Marrakech, Morocco
NP Content: 0.2 %
      Species Name: Tagetes minuta
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Experimental site: Experiment was conducted to study the dry matter content and quality of oil obtained from different plant parts harvested at various growth stages [pre- flowering, 50% flowering, 100% flowering and post-flowering (beginning of seed setting)] at the Central Institute of Medicinal and Aromatic Plants (CIMAP), Lucknow (25.5° N, 80.5° E, 120 m altitude), India. The study area falls in the sub-tropical plains in the northern part of the country. The soil of experimental plot was a sandy loam. Plant material: Tagetes minuta plants were grown in 0.02 ha area during winter season of 2002-2003. Forty day-old seedlings of T. minuta were planted in rows 60 cm apart at 30 cm plant to plat distance within rows in the second week of December, 2002. The crop received fertilizers at the rate of 100 kg N, and 60 kg each of P2O5 and K2O/ha. Nitrogen 40 kg/ha and full quantity of P2O5 and K2O were applied before planting of crop. Remaining of nitrogen application was through topdressing in two equal splits, 30 days after transplanting and at pre-flowering stage. Tagetes minuta plants from 1.20 m row length were harvested from four different places in the experimental area at each date of study. The dates for pre-flowering, 50% flowering, 100% flowering and post-flowering (beginning of seed setting) were March 15, March 27, April 4 and April 18, 2003, respectively.
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               Factor Function
The maximum essential oil yield (1.01 g/plant and 56.1 kg/ha) was obtained upon harvesting at post fowering stage (seed setting stage). Advantage in essential oil yield at this stage was 130%, 34.5% and 36.5% yield enhancement over pre-flowering, 50% and 100% flowering stages, respectively. Flowers and leaves contained the maximum essential oil 2.14% and 1.89% (dry weight basis), respectively. Relative contribution of leaf, flower and stem to essential oil production was 40.7%, 37.8% and 21.5%, respectively. In the oil quality analysis, dihydrotagetone (77.1%) was the predominant component in oil from the leaves while (Z)-beta-ocimene, limonene and (Z)-tagetone were the major constituents in the flower oil. The study suggests that T. minuta should be harvested at the post-flowering stage for realizing maximum essential oil yield and its desirable major chemical constituents. The study also differentiated the quality of leaf and fower oil for chemical constituents.
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               Factor Part Location NP Content
 
Flower: post- flowering stage
Flowers Lucknow, India
NP Content: 1 %
 
Flower: post- flowering stage
Flowers Lucknow, India
NP Content: 2.3 %
 
Flower: 50 % flowering stage
Flowers Lucknow, India
NP Content: 0.9 %
 
Flower: 50 % flowering stage
Flowers Lucknow, India
NP Content: 8.9 %
 
Flower: 100 % flowering stage
Flowers Lucknow, India
NP Content: 3.1 %
 
Leaf: pre-flowering stage
Leaves Lucknow, India
NP Content: 3.4 %
 
Leaf: pre-flowering stage
Leaves Lucknow, India
NP Content: 9.6 %
 
Leaf: 50 % flowering stage
Leaves Lucknow, India
NP Content: 3.7 %
 
Leaf: 50 % flowering stage
Leaves Lucknow, India
NP Content: 4 %
 
Leaf: 100 % flowering stage
Leaves Lucknow, India
NP Content: 1.3 %
 
Leaf: 100 % flowering stage
Leaves Lucknow, India
NP Content: 2.8 %
 
Leaf: post-flowering stage
Leaves Lucknow, India
NP Content: 0.2 %
 
Leaf: post-flowering stage
Leaves Lucknow, India
NP Content: 0.8 %
 
Whole plant: pre-flowering stage
Whole plant Lucknow, India
NP Content: 10 %
 
Whole plant: pre-flowering stage
Whole plant Lucknow, India
NP Content: 4.4 %
 
Whole plant: 50 % flowering stage
Whole plant Lucknow, India
NP Content: 3.8 %
 
Whole plant: 50 % flowering stage
Whole plant Lucknow, India
NP Content: 5.4 %
 
Whole plant: 100 % flowering stage
Whole plant Lucknow, India
NP Content: 2.5 %
 
Whole plant: 100 % flowering stage
Whole plant Lucknow, India
NP Content: 2.6 %
 
Whole plant: post-flowering stage
Whole plant Lucknow, India
NP Content: 0.9 %
 
Whole plant: post-flowering stage
Whole plant Lucknow, India
NP Content: 1.9 %
      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: September) + (Level of fertilization: N2P4K4)
Flowers Plovdiv, Bulgaria
NP Content: 0.4 %
 
Flower: (Harvesting time: September) + (Level of fertilization: N4P2K4)
Flowers Plovdiv, Bulgaria
NP Content: 1.4 %
 
Flower: (Harvesting time: September) + (Level of fertilization: N4P2K4)
Flowers Plovdiv, Bulgaria
NP Content: 2.6 %
 
Flower: (Harvesting time: September) + (Level of fertilization: N4P4K2)
Flowers Plovdiv, Bulgaria
NP Content: 1.6 %
 
Flower: (Harvesting time: September) + (Level of fertilization: N4P4K2)
Flowers Plovdiv, Bulgaria
NP Content: 3.6 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N0P0K0)
Leaves Plovdiv, Bulgaria
NP Content: 5.4 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N0P0K0)
Leaves Plovdiv, Bulgaria
NP Content: 5.8 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N2P4K4)
Leaves Plovdiv, Bulgaria
NP Content: 6.7 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N2P4K4)
Leaves Plovdiv, Bulgaria
NP Content: 7.7 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N4P2K4)
Leaves Plovdiv, Bulgaria
NP Content: 0.9 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N4P2K4)
Leaves Plovdiv, Bulgaria
NP Content: 2.2 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N4P4K2)
Leaves Plovdiv, Bulgaria
NP Content: 2.9 %
 
Leaf: (Harvesting time: July) + (Level of fertilization: N4P4K2)
Leaves Plovdiv, Bulgaria
NP Content: 3.3 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N0P0K0)
Leaves Plovdiv, Bulgaria
NP Content: 3.2 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N0P0K0)
Leaves Plovdiv, Bulgaria
NP Content: 3.8 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N2P4K4)
Leaves Plovdiv, Bulgaria
NP Content: 5.1 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N2P4K4)
Leaves Plovdiv, Bulgaria
NP Content: 9 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N4P2K4)
Leaves Plovdiv, Bulgaria
NP Content: 4.7 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N4P2K4)
Leaves Plovdiv, Bulgaria
NP Content: 7 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N4P4K2)
Leaves Plovdiv, Bulgaria
NP Content: 4.9 %
 
Leaf: (Harvesting time: September) + (Level of fertilization: N4P4K2)
Leaves Plovdiv, Bulgaria
NP Content: 9.4 %
References
1 Effect of the Leaf Drying and Geographic Sources on the Essential Oil Composition of Juniperus thurifera L. var. Africana Maire from the Tensift-Al Haouz, Marrakech Region
2 Essential Oil Quality and Yield with Respect to Harvest Index in Tagetes minuta Cultivated in Sub Tropical Plains of North India
3 Effect of Mineral Fertilization on the Essential Oil Composition of Tagetes patula L. from Bulgaria