General Information of Natural Product (ID: NP0544)
  Natural Product Name
3-Octanone
  Synonyms
3-Octanone; Octan-3-one; 106-68-3; Ethyl amyl ketone; Ethyl pentyl ketone; Amyl ethyl ketone; Ethyl n-pentyl ketone; n-Octanone-3; Ethyl n-amyl ketone; 3-Oxooctane; Ethyl n-amylketone; n-AMYL ETHYL KETONE; 2-Heptanone, methyl-; NSC 60161; EAK; UNII-79173B4107; CHEBI:80946; MFCD00009515; 79173B4107; 3-Octanone (natural); FEMA No. 2803; HSDB 5371; EINECS 203-423-0; UN2271; BRN 1700021; methylheptanone; AI3-36116; CCRIS 8808; 1-ethyl hexanal; 3-octanon; octane-3-one; octan-6-one; 3-Octanone, >=98%; SCHEMBL5593; Ethyl amyl ketone [UN2271] [Flammable liquid]; DSSTox_CID_21954; DSSTox_RID_79883; DSSTox_GSID_41954; WLN: 5V2; 3-Octanone, analytical standard; 3-Octanone, >=98%, FG; CHEMBL2269087; DTXSID3041954; FEMA 2803; NSC60161; ZINC1690036; Tox21_301208; BBL011431; LMFA12000055; NSC-60161; STL146538; AKOS005720776; MCULE-2012071553; NCGC00248338-01; NCGC00255105-01; CAS-106-68-3; VS-02948; 3-Octanone, natural (US), >=97%, FG; FT-0616282; O0122; C17145; A801482; Ethyl amyl ketone [UN2271] [Flammable liquid]; J-001627; Q18349104
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  Formula C8H16O
  Weight 128.21
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3
  InChI Key RHLVCLIPMVJYKS-UHFFFAOYSA-N
  Isomeric SMILES CCCCCC(=O)CC
  Canonical SMILES CCCCCC(=O)CC
  External Links PubChem ID 246728
CAS ID 106-68-3
NPASS ID NPC295442
CHEMBL ID CHEMBL2269087
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Glechoma hederacea
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
Samples of Glechoma hederacea were collected at full flowering in seven localities in Vilnius district (Lithuania) at 2005: A - Salininkai, B -Zolyno, C - Mistunai, D -Antakalnis, E - Nemencine, F - Seskine, G -Zujunai.
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               Factor Function
More than half of the oils were rich in sesquiterpene hydrocarbons (56.5-67.9%). The most predominant compound was germacrene D (14.1-20.7%). The other main constituents were gamma-elemene (9.0-16.0%), beta-elemene (8.7-12.9%), phytols (2.8-15.6%), (Z)-beta-ocimene (2.2-8.5%), 1,8-cineole (92.2-5.4%), beta-ylangene (2.7-4.1%) and germacrene B (2.2-3.9%). Forty-three identified compounds made up 89.1-96.2%. Four oils (A, D-G) might be attributed to germacrene / elemene chemotype and three samples (A-C) containing marked amounts of phytols beside above compounds were of germacrene/elemene/phytols chemotype.
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               Factor Part Location NP Content
 
Locality: Salininkai, Lithuania
Aerial parts Lithuania
NP Content: 0.6 %
 
Locality: Zolyno, Lithuania
Aerial parts Lithuania
NP Content: 0.3 %
 
Locality: Mistunai, Lithuania
Aerial parts Lithuania
NP Content: 0.9 %
 
Locality: Antakalnis, Lithuania
Aerial parts Lithuania
NP Content: 0.7 %
 
Locality: Nemencine, Lithuania
Aerial parts Lithuania
NP Content: 1 %
 
Locality: Seskine, Lithuania
Aerial parts Lithuania
NP Content: 1.8 %
 
Locality: Zujunai, Lithuania
Aerial parts Lithuania
NP Content: 0.9 %
      Species Name: Hyptis pectinata
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
H. pectinutu is an odoriferous plant and occurs as a natural weed on the Fiji Islands and in West Africa as a winter hardy bush. In India, it grows as an erect perrennial shrub in Assam, Bengal and Madras regions. Tlie leaves are ovate and the leaf margins range from crenate to serrate. The flowers are pale purple to yellow in cymose clusters, arranged unilaterally. The nutlets are small, oblong and black.
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               Factor Function
The major compounds present in the Indian oil were sabinene (27.8%), beta-pinene (6.7%), limonene (4.03%), alpha-terpinolene (6.0%), caryopliyllcne (17.2%), alpha-bergamotene (4.1%) and a C20H32-diterpene (5.8%). Other major hydrocarbons present were gamma-terpinene (1.4%), alpha-humulene (1.1%), beta-selinene (1.0%) and gamma-elemene (2.7%). The oil is rather poor in oxygenated terpenoids, the only major oxygen compounds detected were terpinen-4-ol(3.1%), spathulenol(1.1%), an unidentified sesquiterpene alcohol (1.4%) and trans-alpha-bergamotot (2.5%). The total oxygenated compounds constituted about 11% of the oil.
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               Factor Part Location NP Content
 
Locality: India
Whole plant Kumaon, India
NP Content: 0.1 %
      Species Name: Lavandula latifolia
  Factor Name: Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
Plant material: Samples of L. latifolia were collected in August 1998 during the full flowering period (L/La) and in October 1998 during the fruiting period (L/Lb) from three different spike lavender populations located into the Cazorla, Segura y Las Villas Natural Park (Jaen province, Spain). The plant material from each population consisted of the twigs of several single plants. L/La (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: August 14, 1998, Phenological stage: Flowering); L/Lb (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: October 15, 1998, Phenological stage: Fruiting).
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               Factor Function
The small amounts of linalool needed to match the standard can be reached in a natural way (from full flowering to fruiting) which means it is important to choose the most convenient time of harvest in the studied area.
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
Whole plant Spain
NP Content: <0.1 %
 
Whole plant:Fruiting stage
Whole plant Spain
NP Content: 0.1 %
      Species Name: Mentha longifolia
  Factor Name: Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
Plants were collected in the Inner plain, the Sharon plain and the kava valley.
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               Factor Function
The major constituent of all three oils was found to be 1,8-cineole (26.4-34.5%) followed by menthone (10.0-16.7%), pulegone (7.0-7.5%), and isomenthone (4.7-7.8%). Despite some differences in the component proportions, the plants of all three populations clearly belong to the same chemotype.
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               Factor Part Location NP Content
 
Locality: Sharon plain, Israel
Aerial parts Israel
NP Content: 0.2 %
 
Locality: Arava valley, Israel
Aerial parts Israel
NP Content: 0.1 %
 
Locality: Inner plain, Israel
Aerial parts Israel
NP Content: 0.1 %
      Species Name: Nepeta nuda
  Factor Name: Locality Variation; Developmental Stage Variation [5]
              Species Info Factor Info
               Experiment Detail
Biological material for these investigations comes from two distant collection sites: Suva planina (mountain in the east of Serbia) and Durmitor (mountain in Montenegro). All specimens (aerial parts of the plants) were collected in 1994 in the blooming stage and/or in the pre-blooming stage.
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               Factor Function
The results obtained show that though the yields of oils were barely influenced by plant growth stage, they varied appreciably according to the origin of the plant material: pre-blooming, Suva Planina (Serbia): 0.67%; blooming, Suva Planina (Serbia): 0.70%; blooming, Durmitor (Montenegro): 0.40%. Thirty-six components were identified. 1,8-Cineole was always predominant (60%); its concentration was lower (40%) just before blooming. Also present were germacrene D (2-15%), beta-caryophyllene (4-7%), alpha-terpineol (5-7%) and caryophyllene oxides (2-6%). In general, the chemical composition of N. nuda depended more strongly on growth stage than habitat. The only exception was caryophyllene oxide which was three times more abundant in the oil from Montenegro than in that from Serbia.
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               Factor Part Location NP Content
 
Aerial part: Blooming stage + (Locality: Durmito, Montenegro, Yugoslavia)
Aerial parts Yugoslavia
NP Content: 0.1 %
      Species Name: Rosmarinus officinalis
  Factor Name: Developmental Stage Variation [6]
              Species Info Factor Info
               Experiment Detail
Samples of R. officinalis were collected in April 1998 during the full flowering period (Ro-1a), between June and July 1998 during the fruiting period (Ro-1b) and in December 1998 during the hibernation period (Ro-1c) from Cazorla, Segura y Las Villas Natural Park (province of Jaen, Spain). The plant material consisted of ca. 10 twigs per plant (with blossoming tips or not, depending of the harvesting date) from 5-10 single plants. Ro-1a (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: April 21, 1998, Phenological stage: Flowering); Ro-1b (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: June 19, 1998, Phenological stage: Fruiting); Ro-1c (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: December 30, 1998, Phenological stage: Hibernation).
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               Factor Function
The highest oil yields (161.8%) were recorded during the fruiting period (summer). In general, minimum amounts of camphor and maximum amounts of alpha-pinene were observed in winter. The concentration of 1,8-cineole was almost constant throughout the year, though other oil constituent levels varied randomly with the plant life cycle
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
Twigs Las Chozuelas, Southern Spain
NP Content: 2.6 %
 
Whole plant: Fruiting stage
Twigs Las Chozuelas, Southern Spain
NP Content: 1.6 %
 
Hibernation stage
Twigs Las Chozuelas, Southern Spain
NP Content: 3.2 %
      Species Name: Salvia sclarea
  Factor Name: Altitude Variation [7]
              Species Info Factor Info
               Experiment Detail
Clones of T. daenensis populations were collected from 11 locations including seven locations in Fars and four locations in Kohkiluyeh provinces of Iran. The clones of T. daenensis populations were transplanted to the farm at IANRRC Research Station, located in NajafAbad (18 km west Isfahan, 32° 36′ N, 51° 26′ E and 1612 m asl) in March 2002 . Clones were grown in 5 × 2 m plots with 50 × 50 cm planting density. Fertilizers were applied prior to planting at a rate of 60 kg P/ha and 50 kg N/ha. After 3 years (2004), the aerial parts of plants were harvested at full flowering stage, dried at room temperature, and stored until analysis inside paper bags in a cool and dark place. Td1 (Fars Province, Eghlid, Asepas; Altitude: 2000); Td2 (Fars Province, Sourian, Bavanat; Altitude: 2500); Td3 (Fars Province, Abadeh, Keverlar; Altitude: 2280); Td4 (Fars Province, Abadeh -Shiraz Rd, Kolikosh; Altitude: 2400); Td5 (Fars Province, Shiraz -Yasouj Rd, Komehr; Altitude: 2415); Td6 (Fars Province, Yasouj -Shiraz Rd, Margoon; Altitude: 2170); Td7 (Fars Province, Shiraz -Isfahan Rd, Pasargad; Altitude: 2190); Td8 (Kohkiluyeh Province, Sisakht, Gol; Altitude: 2570); Td9 (Kohkiluyeh Province, Kakan; Altitude: 2200); Td10 (Kohkiluyeh Province, Yasouj -Sepidan Rd, Mahparviz; Altitude: 2660); Td11 (Kohkiluyeh Province, Sepidar, Pazanan; Altitude: 2600).
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               Factor Function
Carvacrol, thymol and geraniol were found as the main constituents in the oils of the tested populations. Variation of the oils in populations was subjected to cluster analysis and three different chemotypes including carvacrol (47.3-80.1%), thymol (53.1-72.2%) and geraniol (65.6-75.7%) were identiified. Other important components were beta-caryophyllene (1.7-9%), p-cymene (0.1-10.9%) and gamma-terpinene (0.1-7.8%). Although Thymus is known as having high thymol content in its oil, it is revealed that T. daenensis subsp. daenensis has also a high potential for carvacrol and geraniol constituents in the oil. The largest similarity of the oil components of populations was detected between Td4 and Td7 and the lowest was revealed between Td8 and Td9. The differences in the oil content and composition of the populations could be attributed to their genetic variability and they could be a good genetic source for breeding purposes.
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               Factor Part Location NP Content
 
Locality: Asepas, Eghlid, Fars Province, Iran; Altitude 2000 m
Aerial parts Iran
NP Content: 0.3 %
 
Locality: Bavanat, Sourian, Fars Province, Iran; Altitude 2500 m
Aerial parts Iran
NP Content: 0.7 %
 
Locality: Keverlar, Abadeh, Fars Province, Iran; Altitude 2280 m
Aerial parts Iran
NP Content: < 0.05 %
 
Locality: Kolikosh, Abadeh -Shiraz Rd, Fars Province, Iran; Altitude 2400 m
Aerial parts Iran
NP Content: 2 %
 
Locality: Komehr, Shiraz-Yasouj Rd, Fars Province, Iran; Altitude 2415 m
Aerial parts Iran
NP Content: < 0.05 %
 
Locality: Margoon, Yasouj-Shiraz Rd, Fars Province, Iran; Altitude 2170 m
Aerial parts Iran
NP Content: 0.3 %
 
Locality: Pasargad, Shiraz-Isfahan Rd, Fars Province, Iran; Altitude 2190 m
Aerial parts Iran
NP Content: 0.9 %
 
Locality: Gol, Sisakht, Kohkiluyeh Province, Iran; Altitude 2570 m
Aerial parts Iran
NP Content: 0.6 %
 
Locality: Kakan, Kohkiluyeh Province, Iran; Altitude 2200 m
Aerial parts Iran
NP Content: 0.9 %
 
Locality: Mahparviz, Yasouj -Sepidan Rd, Kohkiluyeh Province, Iran; Altitude 2660 m
Aerial parts Iran
NP Content: 0.4 %
 
Locality: Pazanan, Sepidar, Kohkiluyeh Province, Iran; Altitude 2600 m
Aerial parts Iran
NP Content: 0.3 %
      Species Name: Thymus fontanesii
  Factor Name: Locality Variation; Harvest Time Variation [8]
              Species Info Factor Info
               Experiment Detail
Aerial parts of T. fontanesii were collected during June 2004, in full blossom, in the Province of Tlemcen in four locations: Sidi-snoussi, Remchi, Sebdou et Sebaa-chiouki and again, during June 2005, in the last location.
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               Factor Function
The yield of oil obtained from the aerial parts of Thymus fontanesii harvested in the Province of Tlemcen (Algeria), calculated on dry material basis,varied slightly from station to station: Sebaa-chiouki = 5.20%, Sebdou = 5.25%, Sidisnoussi = 5.32%, Remchi = 5.46%. The composition of the four samples was quite similar, carvacrol (66.7-69.5%) being by far the main component. Other constituents, present at appreciable contents, were p-cymene (6.1-9.1%), gamma-terpinene (6.0-9.6%), linalool (3.0-4.0%), alpha-pinene (2.5-3.0%), myrcene (1.2-1.5%), and alpha-terpinene (1.1-1.4%). Conversely, thymol accounted only for 0.6-0.7% of the composition. Moreover, a sample harvested at Sebaa-chiouki, in June 2005, produced on oil with the same composition (68.3% of carvacrol). Obviously, aerial parts of T. fontanesii from the province of Tlemcen produced an oil whose composition differed substantially from that of the oil obtained from the same species harvested in Setif province and Constantine area (Algeria), dominated by thymol (67.8% and 68.2%, respectively).
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               Factor Part Location NP Content
 
Locality: Remchi, Province of Tlemcen, Algeria + Harvesting time: 2004
Aerial parts Algeria
NP Content: 0.1 %
 
Locality: Sebaa-chiouki, Province of Tlemcen, Algeria + Harvesting time: 2004
Aerial parts Algeria
NP Content: 0.2 %
 
Locality: Sebaa-chiouki, Province of Tlemcen, Algeria + Harvesting time: 2005
Aerial parts Algeria
NP Content: 0.1 %
 
Locality: Sebdou, Province of Tlemcen, Algeria + Harvesting time: 2004
Aerial parts Algeria
NP Content: 0.1 %
 
Locality: Sidi-snoussi, Province of Tlemcen, Algeria + Harvesting time: 2004
Aerial parts Algeria
NP Content: 0.2 %
References
1 The Essential Oil of Ground Ivy (Glechoma hederacea L) Growing Wild In Eastern Lithuania
2 Volatile Constituents of Hyptis pectinata Poit. (Lamiaceae)
3 Chemical Composition and Seasonal Variations of Spike Lavender Oil from Southern Spain
4 Volatile Extract of Mentha longifolia Growing in Israel. Aromatic Plants of the Holy Land and the Sinai. Part XIII
5 Quantity and Composition of Essential Oil of the Wild Plant Nepeta nuda L. from Yugoslavia
6 Chemical Composition and Seasonal Variations of Rosemary Oil from Southern Spain
7 Essential Oil Variation in Hyptis marrubioides subsp. daenensis Cleak Populations
8 Composition and Antibacterial Activity of the Essential Oil of Thymus fontanesii Boiss. et Reut. from Algeria.