General Information of Natural Product (ID: NP0293)
  Natural Product Name
1,3,3-Trimethyl-2-Oxabicyclo[2.2.2]Oct-5-Ene
  Synonyms
2,3-Dehydro-1,8-cineole; Dehydrocineole; Dehydro-1,8-cineol; Dehydro-1,8-cineole; 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene; 1,8-Dehydrocineole; 1,8-cineole dehydro; Dehydro-1,8-cyneole; Dehydro-1.8-cineole; 2,3-Dehydro-1,8-cineol; 1,8-Epoxy-p-menth-2-ene; 1,8-Epoxy-p-mentha-2-ene; 66113-06-2; SCHEMBL23358702; DTXSID80335140; CHEBI:167365; 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene #; Q67879829; 92760-25-3
Click to Show/Hide
  Formula C10H16O
  Weight 152.23
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H16O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h4,6,8H,5,7H2,1-3H3
  InChI Key LOOYOTLEOHYYOV-UHFFFAOYSA-N
  Isomeric SMILES CC1(C2CCC(O1)(C=C2)C)C
  Canonical SMILES CC1(C2CCC(O1)(C=C2)C)C
  External Links PubChem ID 523035
CAS ID 66113-06-2

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [1]
              Species Info Factor Info
               Experiment Detail
Populations of A. annua cultivar 'Jeevanraksha' and accession Suraksha were grown in the experimental field plot of the Institute at New Delhi. The seeds were sown in January 2004, seedlings transplanted in late February 2004 and aerial parts (flowers, leaves and stems from the upper 0.5 m of crop canopy) sampled in late October 2004.
Click to Show/Hide
               Factor Function
Ninety-seven compounds comprising 91.3% of the total oil of 'Jeevanraksha' were identified. Forty-three monoterpenes (56.6%), 32 sesquiterpenes (31.1%), and 2 diterpenes (0.2%) comprised bulk of the oil (87.9%). The oil was devoid of artemisia ketone and contained camphor (13.5%), 1,8-cineole (9.4%), trans-sabinol (7.1%), p-mentha-1(7), 5-dien-2-ol (6.3%), myrcene (4.7%), germacrene D (4.4%), (E)-beta-farnesene (3.9%), beta-caryophyllene (3.7%), dihydroartemisinic lactone (3.0%) and p-cymene (2.0%) as the major constituents. Eighty-six compounds representing 93.3% of the composition were identified in the Suraksha oil. This oil contained artemisia ketone (47%), 1,8-cineole (8.4%), camphor (5.9%) and alpha-pinene (5.2%) as the major components.
Click to Show/Hide
               Factor Part Location NP Content
 
Artemisia annua accessions Suraksha
Aerial parts India
NP Content: 0.3 %
 
Artemisia annua cv. Jeevanraksha
Aerial parts India
NP Content: 0.1 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [2]
              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.
Click to Show/Hide
               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.
Click to Show/Hide
               Factor Part Location NP Content
 
Salvia euphratica var. euphratica
Flowering aerial parts Turkey
NP Content: < 0.1 %
 
Salvia euphratica var. leiocalycina
Flowering aerial parts Turkey
NP Content: < 0.1 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
Plant material and isolation procedure: Aerial parts of the plant were collected from two regions, from Kazeroon in southern Iran and Shahr-e-kord in western Iran at the time of flowering in June 2002.
Click to Show/Hide
               Factor Function
The main components of the oil of S. pilifera collected from Kazeroon, in southern Iran, were spathulenol (15.8%), cis-chrysanthenol (15.3%), beta-caryophyllene (8.4%) and cis-chrysanthenyl acetate (6.9%), while for the plant collected from Shahr-e-kord, in western Iran, they were cis-chrysanthenyl acetate (21.8%), linalool (18.9%), terpinen-4-ol (11.9%) and cis-chrysanthenol (9.2%).
Click to Show/Hide
               Factor Part Location NP Content
 
Locality: Kazeroon, southern Iran
Aerial parts Iran
NP Content: 0.3 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [4]
              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.
Click to Show/Hide
               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%).
Click to Show/Hide
               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 %
 
Flower: (Locality: Sivas, Turkey)
Flowers Sivas, Turkey
NP Content: 0.2 %
 
Stem: (Locality: Sivas, Turkey)
Stems Sivas, Turkey
NP Content: 0.1 %
      Species Name: Thymus carnosus
  Factor Name: Month Variation; Developmental Stage Variation [5]
              Species Info Factor Info
               Experiment Detail
The aerial parts of samples from collective populations of T. carnosus were collected during the vegetative phase (February 2000), at the beginning of the flowering phase (May 2000) and during the flowering phase (July 2000) at Quinta do Lago (Algarve). AQLM: collected in May, beginning of flowering phase; AQLJ: collected in July, flowering stage; AQLF: collected in Feb, vegetative stage.
Click to Show/Hide
               Factor Function
All the oil samples collected in Quinta do Lago (QL) were dominated by borneol (26-31%) and camphene (9-18%), but the third main component varied according to the harvesting period. Bornyl acetate was the third main component (9-13%) in the flower oil and in the aerial parts oils collected in May and July, whereas terpinen-4-ol (8%) was the third main component in oil collected in February from vegetative phase plant material. A fourth main component, alpha-pinene (4-9%), was also present in relative high amounts in the QL oils.
Click to Show/Hide
               Factor Part Location NP Content
 
Harvesting time: Feb, vegetative stage
Aerial parts Quinta do Lago, Portugal
NP Content: <0.05 %
 
Harvesting time: May, beginning of flowering satge
Aerial parts Quinta do Lago, Portugal
NP Content: <0.05 %
 
Harvesting time: July, flowering stage
Aerial parts Quinta do Lago, Portugal
NP Content: 0.1 %
 
Harvesting time: July, flowering stage
Flowers Quinta do Lago, Portugal
NP Content: 0.1 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [6]
              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
Click to Show/Hide
               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.
Click to Show/Hide
               Factor Part Location NP Content
 
Locality: Karadere, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: <0.1 %
References
1 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
2 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
3 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
4 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
5 Thymus carnosus Boiss.: Effect of Harvesting Period, Collection Site and Type of Plant Material on Essential Oil Composition
6 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey