General Information of Natural Product (ID: NP0670)
  Natural Product Name
Alpha-Campholenal
  Synonyms
alpha-Campholenal; 4501-58-0; [(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]acetaldehyde; 2-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]acetaldehyde; (+)-campholenic aldehyde; (R)-alpha-campholenaldehyde; UNII-75LU5216DI; (R)-(+)-campholenic aldehyde; CHEBI:49150; 75LU5216DI; 3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-, (1R)-; (R)-2,2,3-Trimethyl-3-cyclopentene-1-acetaldehyde; alpha-Campholene aldehyde; (R)-2,2,3-Trimethylcyclopent-3-ene-1-acetaldehyde; Campholenal, alpha-; (R)--campholenaldehyde; Campholenaldehyde, alpha-; (R)-2-(2,2,3-Trimethylcyclopent-3-en-1-yl)acetaldehyde; 3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-, (R)-; DSSTox_CID_24756; DSSTox_RID_80449; DSSTox_GSID_44756; FEMA No. 3592; CHEMBL3184714; DTXSID3044756; SCHEMBL15316770; ZINC1063075; EINECS 224-815-8; Tox21_301648; AKOS006239754; 2,2,3-Trimethyl-3-cyclopentacetaldehyde; NCGC00256080-01; CAS-4501-58-0; AI3-23129; EC 224-815-8; Q27121498; 2,2,3-Trimethyl-3-cyclopentene-1-acetaldehyde, (R)-
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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/c1-8-4-5-9(6-7-11)10(8,2)3/h4,7,9H,5-6H2,1-3H3/t9-/m1/s1
  InChI Key OGCGGWYLHSJRFY-SECBINFHSA-N
  Isomeric SMILES CC1=CC[C@@H](C1(C)C)CC=O
  Canonical SMILES CC1=CCC(C1(C)C)CC=O
  External Links PubChem ID 1252759
CAS ID 4501-58-0
NPASS ID NPC95581
CHEMBL ID CHEMBL3184714
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia verlotiorum
  Factor Name: Developmental Stage Variation [1]
              Species Info Factor Info
               Experiment Detail
Plant material of A. verlotiorum was harvested near Marseille (France) in May (before blooming) and November (full flowering) 2000.
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               Factor Function
For the oil from the vegetative plants, 50 compounds, representing 99.8% of the oil were characterized. Fifty-nine compounds, representing 99.6% of the oil were identified in the oil from flowering plants. In both cases, the constituents were mainly oxygenated monoterpenes (74% and 88%). The composition of each oil showed only a few differences, as the main components were alpha-thujone (55% and 44%), 1,8-cineole (5% and 15%), beta-caryophyllene (13% and 7%) and beta-thujone (5% and 11%), in the oils of the vegetative plant and flowering plant, respectively. The proportions of the oxygenated compounds seemed to increase during flowering.
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               Factor Part Location NP Content
 
Aerial part: before blooming stage
Aerial parts Marseille, France
NP Content: 0.1 %
 
Aerial part: full flowering stage
Aerial parts Marseille, France
NP Content: 0.1 %
      Species Name: Eucalyptus grandis
  Factor Name: Seasonal Variation [2]
              Species Info Factor Info
               Experiment Detail
Eucalyptus urophylla and E. grandis were collected in January (summer) and August (winter) 2006 at the mature vegetative state from Goiania city Brazil, and identified by one of the authors (E.P.F.). Leaves from 5-11 randomized individual plants of the same age representing the local population were collected as homogenous samples in each season, dried at room temperature.
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               Factor Function
The results were submitted to Principal Components and Clusters Analysis which enabled four groups of oils to be distinguished with regard to specimens and harvest seasons: clusters I and II with only E. grandis samples collected in the cold and dry winter and the hot and humid summer, which were characterized by a high percentage of isoleptospermone (9.6% and 13.2%), alpha-pinene (12.2% and 24.7%), p-cymene (20.5% and 14.5%), and alpha-terpineol (14.3% and 4.9%), respectively; clusters III and IV only associated with E. urophylla samples collected in summer and winter with 1,8-cineole (36.6% and 44.7%) and alpha-terpinyl acetate (7.0% and 11.7%) rich oils.
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               Factor Part Location NP Content
 
Harvesting time: Summer
Whole plant Brazil
NP Content: 1.5 %
 
Harvesting time: Winter
Whole plant Brazil
NP Content: 1.9 %
      Species Name: Sphagneticola trilobata (L.)
  Factor Name: Seasonal Variation [3]
              Species Info Factor Info
               Experiment Detail
Fresh aerial parts of the S. trilobata were collected from CSIR-Central Institute of Medicinal and Aromatic Plants, Research Centre Pantnagar (Uttarakhand) in summer (vegetative stage), rainy (vegetative stage), autumn (flowering stage) and winter (flowering stage) seasons. The experimental site is located between coordinates 29.02° N, 79.31° E and an altitude of 243 m in foothills of northern India.
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               Factor Function
Volatile oil yield varied from 0.18 to 0.25% in different seasons, with the maximum in winter season. Altogether, 43 constituents, representing 96.1-97.3% of the total oil composition were identified. Major constituents of the oils were alpha-pinene (78.6-83.3%), alpha-phellandrene (1.3-4.1%), sabinene (1.4-1.9%), limonene (1.2-1.9%), beta-pinene (1.0-1.6%), camphene (0.7-2.0%), 10-nor-calamenen-10-one (<0.05-1.5%), germacrene D (0.1-1.4%) and gamma-amorphene (<0.05-1.3%). The comparative results showed no big differences in the oil composition of this plant due to season of collection.
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               Factor Part Location NP Content
 
Harvesting time: Summer
Aerial parts India
NP Content: 0.1 %
 
Harvesting time: Autumn
Aerial parts India
NP Content: <0.05 %
 
Harvesting time: Winter
Aerial parts India
NP Content: <0.05 %
 
Harvesting time: Rainy
Aerial parts India
NP Content: <0.05 %
      Species Name: Teucrium flavum
  Factor Name: Month Variation; Developmental Stage Variation [4]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. flavum were collected in different periods from December to July 2006, from plants growing along the Ionic coast of Sicily (Italy). LF 1-LF 2-LF 3: represent the composition of leaf oils of plant samples collected in December (vegetative stage), February (pre-flowering stage) and April (budding stage) respectively; FL: flower oil; FR: fruit oil.
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               Factor Function
Some components, in all investigated plant parts, remained more or less constant during all the different phases of the plant cycle life. Worthy of note, considering the leaf oils, was that beta-pinene, limonene and germacrene D increased in the pre-flowering stage, while a series of esters and alpha-copaene, beta-caryophyllene, viridiflorol, Tmuurolol and phytol increased in the budding stage (LF3); the vegetative stage oil is generally characterized by a rich chemical composition and some constituents such as isoamyl hexanoate, alpha-humulene, bicyclogermacrene, beta-bisabolene and alpha-bisabolol reached their highest levels in this oil. In the flower oil, linalool and 1-octen-3-yl acetate were the main components compared to the amounts found in the other oils. Fruit oil composition was relatively oil poor, with beta-bisabolene, caryophyllene oxide, cadin-4-en-1-ol and phytone as the major constituents.
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               Factor Part Location NP Content
 
Harvesting time: April; budding stage
Leaves Italy
NP Content: <0.01 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Aerial parts of the plant were collected from four localities: A = Kirklareli: Karadere in May 1991; B = Kirklareli: Karahamza Village in May 1990; C = Kirklareli: Evciler Village on 13 June 1993; D = Kirklareli: Korukoy on 25 May 1994
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               Factor Function
The four oils obtained from plants collected in different localities of the same region gave quite different compositions as follows: A: thymol (10.5%), 1,8-cineole (9.96%), p-cymene (9.48%), carvacrol (5.28%); B: beta-caryophyllene (29.50%), carvacrol(20.59%); C: thymol (34.7%), beta-caryophyllene (12.74%), carvacrol (5.24%); D: beta-caryophyllene (56.48%), germacrene D (11.12%), carvacrol (4.85%). Since the identities of the plant materials were checked repeatedly, any misidentification is ruled out. Except for A and C, all the other materials showed beta-caryophyllene as the major constituent. Carvacrol (20.59%) was present in good amount in the oil of B. In A, however, high percentages of 1,8-cineole (10%) and p-cymene (9.5%) were significant. This oil contained only a trace amount of beta-caryophyllene. Four isomeric caryophyllene alcohols were detected in the oil B. The results clearly indicate that the oil of T. striatus var. interruptus has no consistency and we can safely suggest that there are at least three chemotypes, namely thymol/1,8-cineole/p-cymene-type; thymol/beta-caryophyllene-type; and beta-caryophyllene-type, of this species.
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               Factor Part Location NP Content
 
Locality: Karadere, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: <0.1 %
References
1 Chemical Variation in the Oil of Artemisia verlotiorum Lamotte of French Origin Harvested at a Vegetative Stage and During Flowering
2 Seasonal Influence on the Essential Oil Compositions of Eucalyptus urophylla S. T. Blake and E. grandis W. Hill ex Maiden from Brazilian Cerrado
3 Essential oil composition of Sphagneticola trilobata (L.) Pruski from India
4 Seasonal Variations of Teucrium flavum L. Essential Oil
5 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey