General Information of Natural Product (ID: NP0082)
  Natural Product Name
Alpha-Calacorene
  Synonyms
alpha-Calacorene; 21391-99-1; DTXSID201020798; Naphthalene,1,2-dihydro-4,7-dimethyl-1-(1-methylethyl)-, (1S)-; ZINC85600895; (S)-1-Isopropyl-4,7-dimethyl-1,2-dihydronaphthalene; (1S)-4,7-dimethyl-1-propan-2-yl-1,2-dihydronaphthalene
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  Formula C15H20
  Weight 200.32
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H20/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-7,9-10,13H,8H2,1-4H3/t13-/m0/s1
  InChI Key CUUMXRBKJIDIAY-ZDUSSCGKSA-N
  Isomeric SMILES CC1=CC[C@H](C2=C1C=CC(=C2)C)C(C)C
  Canonical SMILES CC1=CCC(C2=C1C=CC(=C2)C)C(C)C
  External Links PubChem ID 12302243
CAS ID 21391-99-1

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Bocageopsis multiflora
  Factor Name: Seasonal Variation [1]
              Species Info Factor Info
               Experiment Detail
Bocageopsis multiflora leaves were collected in the Adolpho Ducke reserve, Km 26 Manaus - Itacoatiara highway, in the State of Amazonas, Brazil. This species was collected in the rainy (April 2010) and dry seasons (September 2010).
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               Factor Function
The main constituent of the oil collected in the rainy season was bisabolene (13.2%), while the main constituent in the dry season was spathulenol (16.2%). The highest yield (0.3%) was obtained for the oil collected in the rainy season.
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               Factor Part Location NP Content
 
Harvesting time: Rainy season
Leaves Brazil
NP Content: 1 %
 
Harvesting time: Dry season
Leaves Brazil
NP Content: 0.8 %
      Species Name: Helichrysum arenarium
  Factor Name: Locality Variation; Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
The plant material was collected in eastern Lithuania (July-August, 2002). Numbers of growing localities of H. arenarium with yellow (Y) and orange (O) flowers were as follows: Svencionys district (Zalavas) and Ukmerge district (Sventupe).
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               Factor Function
The 68 constituents identified comprised 73.8-90.7% of the total oil content. It was found that the principal constituents were: beta-caryophyllene (in three inflorescence and one leaf oil), delta-cadinene (in two leaf oils), octadecane (in one leaf oil) and heneicosane (in one inflorescence sample). Monoterpenes and oxygenated monoterpenes made up 4.0-13.9%, aliphatic hydrocarbons 0.4-35.3%, and sesquiterpenes 24.7-71.2% of the oils.
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               Factor Part Location NP Content
 
Inflorescence: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.2 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 1 %
 
Inflorescence: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 1.4 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 1.5 %
 
Leaf: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.6 %
 
Leaf: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 3 %
 
Leaf: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 1.6 %
 
Leaf: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 1.5 %
      Species Name: Mentha rotundifolia
  Factor Name: Altitude Variation [3]
              Species Info Factor Info
               Experiment Detail
Mentha rotundifolia leaves were collected in the second week of November 2004 in two localities of Algeria (Rouina: altitude 250 m, Miliana: altitude 780 m) within the region of Ain-Defla located in northern Algeria.
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               Factor Function
Thirty-nine compounds were identified in leaf oil of sample 1 (Rouina, Algeria), the main one being cis-piperitone oxide. Thirty-nine compounds were identified in leaf oil of sample 2 (Miliana, Algeria). The main one being piperitenone oxide.
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               Factor Part Location NP Content
 
Locality: Miliana, Algeria; Altitude 780 m
Leaves Algeria
NP Content: < 0.1 %
      Species Name: Persea americana
  Factor Name: Variety Comparison; Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
Experimental: Two hundred grams of healthy mature intact leaves were harvested from each of the taxa growing on their own rootstocks at the UC South Coast Research and Extension Center. flocc = P. americana var. floccosa from Mexico D-7; stey = P. americana var. steyermarkii from Mexico El Salvador 3-22-16; nubi = P. americana var. nubigena from Guatemala 45-C-1; mex = P. americena var. drymfolia from Tasco, Mexico; guat = P. americana var. guatemalensis cult. Nimlioh from Florida; bwl = P. ameticana var. americana cult. Trapp from Florida.
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               Factor Function
Analysis of oils showed the presence of over 90 components, of which 76 were identified. P. schiedeana oil was found to contain alpha-pinene (23.7%), beta-pinene (23.2%) and beta-caryophyllene as major components. The major constituents of P. americana var. floccosa and P. americana var. steyermarkii were alpha-pinene (10.9%, 7.6%), beta-pinene (20.6%, 10.4%), alpha-terpineol (9.6%, 7.9%), beta-caryophyllene (12.6%, 8.4%), viridiflorene (0.1%, 10.3%) and globulol (0.1%, 9.2%), respectively. The oils of P. americana var. nubigena and P. americana var. drymifolia contained alpha-terpineol (18.4%, 393%) and methylchavicol (12.4%, 40.2%), as major components, respectively. P. americana var. guatemalensis was found to be rich in beta-caryophyllene (38.3%), while the oils of P. americana var. americana and P. primatogena contained alpha-pinene (27.5%) and beta-pinene (40.9%), and alpha-pinene (24.6%), beta-caryophyllene (20.7%) and germacene D (10.1%).
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               Factor Part Location NP Content
 
Persea americana var. drymfolia (Locality: Tasco)
Leaves Tasco, Mexico
NP Content: 0.01 %
 
Persea americana var. nubigena (Locality: Guatemala)
Leaves Guatemala
NP Content: 0.01 %
      Species Name: Rosmarinus officinalis
  Factor Name: Developmental Stage Variation [5]
              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: 0.1 %
 
Whole plant: Fruiting stage
Twigs Las Chozuelas, Southern Spain
NP Content: <0.1 %
 
Hibernation stage
Twigs Las Chozuelas, Southern Spain
NP Content: <0.1 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected during the flowering period in July 2002 from the Dumluca Mountain in the vicinity of Divrigi village of Sivas city at 1900 m altitude and Saksagan Gorge in Saimbeyli village of Adana city at 1900 m altitude.
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               Factor Function
The flower, stem and root oils of T. cadmeum ssp. orientale collected from the Adana location were characterized with alpha-thujone (25%, 5.2%), cis-linalool oxide (6.8%, 12.8%), trans-chrysanthenyl acetate (5.8%, 8.5%) for flower and stem oils, and beta-eudesmol (10.3%, 6.2%, 13.8%); in addition, stem oil contained 1,8-cineole (6.6%) and root oil contained hexadecanoic acid (6.0%), spathulenol (5.8%) and beta-muurolol (5.3%). The flower and stem oils of T. cadmeum ssp. orientale collected from the Sivas location were characterized with camphor (25.9%, 14.8%), borneol (15.4%, 25.8%) and alpha-thujone (7.8%, 5.5%); in addition, stem oil contained 1,8-cineole (7.4%) and root oil contained nonacosane (16.2%), spathulenol (6.8%) and hexadecanoic acid (5.8%).
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               Factor Part Location NP Content
 
Flower: (Locality: Adana, Turkey)
Flowers Adana, Turkey
NP Content: 0.1 %
 
Stem: (Locality: Adana, Turkey)
Stems Adana, Turkey
NP Content: <0.1 %
 
Root: (Locality: Adana, Turkey)
Roots Adana, Turkey
NP Content: 0.1 %
 
Root: (Locality: Sivas, Turkey)
Roots Sivas, Turkey
NP Content: 0.2 %
      Species Name: Tanacetum dolichophyllum
  Factor Name: Altitude Variation [7]
              Species Info Factor Info
               Experiment Detail
Wild growing Tanacetum dolichophyllum samples were collected during the period of full flowering, between September-October 2009 from high alpine meadows of Western Himalaya (Uttarakhand, India): Sample I (Dayara, altitude 3200 m) and Sample II (Tungnath, altitude 3800 m).
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               Factor Function
Plant collected from Dayara meadow (Sample I) afforded cis-lanceol (11.8%), beta-pinene (10.7%), (E)- beta-farnesene (7.4%), alpha-bisabolol (7.2%), beta-eudesmol (5.2%) and terpinen-4-ol (5.1%) as the major constituents, whereas in the sample collected from Tungnath (Sample II) beta-eudesmol (31.4%), alpha-bisabolol (10.7%) were the most abundant components followed by neryl acetate (5.8%) and (E)-beta-farnesene (5.7%). The composition was dominated by sesquiterpene hydrocarbons and oxygen containing sesquiterpenes (49.2-71.1%). The oils are clearly different from those of all other previously reported T. dolichophyllum oils.
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               Factor Part Location NP Content
 
Locality: Dayara; Altitude 3200m
Aerial parts Himalyas, Uttarakhand, India
NP Content: 0.9 %
      Species Name: Teucrium flavum
  Factor Name: Month Variation; Developmental Stage Variation [8]
              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
 
Flower oil
Flowers Italy
NP Content: 0.2 %
      Species Name: Vitis vinifera
  Factor Name: Variety Comparison [9]
              Species Info Factor Info
               Experiment Detail
Grape pomaces and stalks of Nero d'Avola and Frappato were donated by the ''Valle dell'Acate'' wine firm, Acate, RG, Italy - those from Nerello Mascalese and Cabernet Sauvignon were given by the ''Emanuele Scammacca Barone del Murgo'' wine firm, Santa Venerina, CT, Italy. The winemaking procedures were similar for all samples, namely grape clusters were crushed and destemmed using a destemmer-crusher. The crushed grapes were treated with sulphur dioxide (0.2-0.5% total mash) and with selected strains of Saccharomyces cerevisiae to start up the fermentation. After 6-8 days of maceration, when alcoholic fermentation was finished, the mash was pressed. Stalks coming from destemming procedure and grape pomace coming from the maceration procedure were subjected to the distillation procedures within 24 h of their collection. All materials were collected during the 2004 vintage.
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               Factor Function
On the whole, 38 components have been characterized in the samples of grape pomaces, with Frappato cv. showing the richest composition; instead, 88 components have been detected in the stalks of Frappato, Nero d'Avola, Nerello Mascalese and Cabernet Sauvignon varieties.
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               Factor Part Location NP Content
 
Vitis vinifera var. Cabernet Sauvignon
Stalks Italy
NP Content: 0.74 %
 
Vitis vinifera var. Frappato
Stalks Italy
NP Content: 0.38 %
 
Vitis vinifera var. Nerello Mascalese
Stalks Italy
NP Content: 0.74 %
 
Vitis vinifera var. Nero d'Avola
Stalks Italy
NP Content: < 0.05 %
References
1 Chemical composition and biological activities of Bocageopsis multiflora essential oil
2 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
3 Chemical Composition of the Leaf Oil of Mentha rotundifolia (L.) from Algeria
4 Essential Oils of Persea subgenus Persea (Lauraceae)
5 Chemical Composition and Seasonal Variations of Rosemary Oil from Southern Spain
6 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
7 Variation in the Constituents of Tanacetum dolichophyllum (Kitam.) Kitam. from Different Locations of Uttarakhand Himalaya (India)
8 Seasonal Variations of Teucrium flavum L. Essential Oil
9 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.