General Information of Natural Product (ID: NP0326)
  Natural Product Name
Isopinocamphone
  Synonyms
(-)-Isopinocamphone; Isopinocamphone; 14575-93-0; (1S,2S,5R)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-3-ONE; [1S-(1alpha,2beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one; (1S-(1alpha,2beta,5alpha))-2,6,6-Trimethylbicyclo(3.1.1)heptan-3-one; S-pinocamphone; Bicyclo(3.1.1)heptan-3-one, 2,6,6-trimethyl-, (1R,2R,5S)-rel-; cis-3-pinanone; (?)-Pinocamphone; EINECS 238-619-5; EINECS 239-394-6; EINECS 250-212-4; SCHEMBL15210011; DTXSID30881208; CHEBI:171987; Bicyclo[3.1.1]heptan-3-one, 2,6,6-trimethyl-, (1alpha,2beta,5alpha)-; Q27286945; UNII-Q366628FXX component MQPHVIPKLRXGDJ-RNJXMRFFSA-N; (1)-(1alpha,2beta,5alpha)-2,6,6-Trimethylbicyclo(3.1.1)heptan-3-one
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  Formula C10H16O
  Weight 152.23
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-8H,4-5H2,1-3H3/t6-,7+,8-/m0/s1
  InChI Key MQPHVIPKLRXGDJ-RNJXMRFFSA-N
  Isomeric SMILES C[C@H]1[C@@H]2C[C@@H](C2(C)C)CC1=O
  Canonical SMILES CC1C2CC(C2(C)C)CC1=O
  External Links PubChem ID 84532
CAS ID 14575-93-0

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Eucalyptus camaldulensis
  Factor Name: Variety Comparison [1]
              Species Info Factor Info
               Experiment Detail
Fresh leaves of the E. camaldulensis varieties(var. mysore and var. Catharine) were collected from 12 mature trees growing in Agodi Gardens, Ibadan, Nigeria.
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               Factor Function
The quantitatively significant constituents in die leaf oil of the two E. camaldulensis varieties were beta-pinene (9.0-17.5%), 1,8-cineole (32.8-70.4%), (Z)-beta-ocimene (11.6%) and alpha-pinene (8.8%). Monoterpenoids also made up the bulk of the two volatile oils (89.0-95.7%).
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               Factor Part Location NP Content
 
Eucalyptus camaldulensis var. mysore
Leaves Nigeria
NP Content: 0.2 %
      Species Name: Hyssopus officinalis
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
H. officinalis var. dectimbens was grown on Banon (Alpes de Haute-Provence, France). The fresh flowering tops were steam distilled at the beginning of October 1995. A sample of H. officinalis oil produced in Italy (Piedmont) by Agronatura was examined as a useful standard in accordance with the IS0 9841 Standard (1991 E).
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               Factor Function
The bicyclic monoterpene ketones, pinocamphone and isopinocamphone, were present in Piedmont, Italy (4.4% and 43.3%, respectively, in accordance with the ISO 9841 Standard, 1991 E), but their percentages were very low in Banon, France, where instead linalool (49.6%), 1,8-cineole (13.3%) and limonene (5.4%) were predominant.
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               Factor Part Location NP Content
 
Locality: Banon, France
Flowers Banon, France
NP Content: 1.3 %
 
Locality: Piedmont, Italy
Flowers Piedmont, Italy
NP Content: 43.3 %
      Species Name: Rosamarinus officinalis
  Factor Name: Month Variation; Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
The plants from Shawieh were harvested four times in 1998 on different separate plants: at full flowering (March), after flowering (May) and at late flowering season (November). And in 1999 at full flowering (March).
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               Factor Function
The oil samples were found to be rich in alpha-pinene (18.8-38.5%) and 1,8-cineole (19.1-25.1%). The Lebanese oils had particularly high levels of alpha-terpineol (2.9-11.2%) and geraniol (1.8-9.3%). The maximum alpha-pinene content is related to flowering period. Although the results obtained did not indicate a large variation of oil composition in relation to harvest time (flowering and after flowering), some reproducible differences were noticeable.
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               Factor Part Location NP Content
 
Whole plant: flowering stage + Harvesting time: March-1998
Whole plant Shaweih, Lebanon
NP Content: 0.2 %
 
Whole plant: after flowering stage + Harvesting time: May-1998
Whole plant Shaweih, Lebanon
NP Content: 0.4 %
 
Whole plant: late flowering stage + Harvesting time: November-1998
Whole plant Shaweih, Lebanon
NP Content: 0.3 %
 
Leaves: flowering stage + Harvesting time: March-1999
Leaves Shaweih, Lebanon
NP Content: 0.2 %
      Species Name: Rosmarinus officinalis
  Factor Name: Developmental Stage Variation [4]
              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: 0.2 %
 
Whole plant: Fruiting stage
Twigs Las Chozuelas, Southern Spain
NP Content: 0.2 %
 
Hibernation stage
Twigs Las Chozuelas, Southern Spain
NP Content: 0.1 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [5]
              Species Info Factor Info
               Experiment Detail
Aerial parts of both varieties(Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and Salvia euphratica Montbret et Aucher ex Benth. var. leiocalycina) were collected in Malatya, Turkey in June 1999.
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               Factor Function
Ninety-five compounds in var. euphratica and 94 compounds in var. leiocalycina were characterized representing 93% and 95% of the total components detected, respectively, with 1,8-cineole (13.8% and 15.2%) and myrtenyl acetate (15.9% and 13.9%) as main constituents.
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               Factor Part Location NP Content
 
Salvia euphratica var. leiocalycina
Flowering aerial parts Turkey
NP Content: 0.3 %
References
1 Essential Oil Composition of Two Varieties of Eucalyptus camaldulensis Dehn. from Nigeria
2 A Pinocamphone Poor Oil of Hyssopus officinalis L. var. decumbens from France (Barton)
3 Chemical Composition of Lebanese Rosemary (Rosmarinus officinalis L.) Essential Oil as a Function of the Geographical Region and the Harvest Time
4 Chemical Composition and Seasonal Variations of Rosemary Oil from Southern Spain
5 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey