Details of Natural Product (NP)

General Information of Natural Product (ID: NP0678)
  Natural Product Name
Cis-3-Hexenyl Isovalerate
  Synonyms
cis-3-Hexenyl isovalerate; 35154-45-1; (Z)-3-Hexenyl isovalerate; (Z)-Hex-3-enyl isovalerate; [(Z)-hex-3-enyl] 3-methylbutanoate; (Z)-3-Hexen-1-yl isovalerate; cis-3-Hexenyl isopentanoate; 3-Hexenyl isovalerate; 3-Hexenyl isopentanoate; Hex-3-enyl isovalerate; (Z)-Hex-3-en-1-yl 3-methylbutanoate; (Z)-3-Hexenyl 3-methylbutyrate; Isovaleric acid, 3-hexenyl ester; (Z)-3-hexenyl 3-methylbutanoate; cis-Hex-3-enyl 3-methylbutanoate; AI3-35966; (Z)-Hex-3-enyl 3-methylbutanoate; Isovaleric acid cis-3-hexenyl ester; 3-Hexenyl 3-methylbutanoate; cis-3-Hexenyl 3-methylbutanoate; UNII-L9KN8775G8; Butanoic acid, 3-methyl-, (3Z)-3-hexenyl ester; 3-Hexen-1-yl 3-methylbutanoate; Butanoic acid, 3-methyl-, 3-hexenyl ester, (Z)-; (Z)-3-Hexenyl isopentanoate; Butanoic acid, 3-methyl-, 3-hexen-1-yl ester; ISOVALERIC ACID, 3-HEXENYL ESTER, (Z)-; L9KN8775G8; (3Z)-3-Hexenyl 3-methylbutanoate; Butanoic acid, 3-methyl-, (3Z)-3-hexen-1-yl ester; Butanoic acid, 3-methyl-, 3-hexenyl ester; WE(6:1(3Z)/4:0(3Me)); EINECS 252-404-3; BRN 2433447; FEMA No. 3498; 3-Hexenyl isovalerate, (3Z)-; EINECS 233-104-1; 3Z-Hexenyl Isovalerate; cis-3-Hexenyl iso-valerate; (3Z)-HEX-3-EN-1-YL 3-METHYLBUTANOATE; (3Z)-3-hexenyl isovalerate; SCHEMBL573191; DTXSID2052029; AIQLNKITFBJPFO-WAYWQWQTSA-; FEMA 3498; CHEBI:172060; AMY40648; 3-Hexenyl ester(Z)-Isovaleric acid; LMFA07010592; MFCD00036533; ZINC12153709; [(E)-hex-3-enyl] 3-methylbutanoate; Isovaleric acid cis-3-hexen-1-yl ester; 3-Methyl-3-hexenyl ester(Z)-Butanoic acid; I0307; cis-3-Hexenyl Isovalerate FCC, No Antioxidant; A874733; cis-3-Hexenyl 3-methylbutanoate, >=97%, FCC, FG; Q27282877
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  Formula C11H20O2
  Weight 184.27
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C11H20O2/c1-4-5-6-7-8-13-11(12)9-10(2)3/h5-6,10H,4,7-9H2,1-3H3/b6-5-
  InChI Key AIQLNKITFBJPFO-WAYWQWQTSA-N
  Isomeric SMILES CC/C=C\\CCOC(=O)CC(C)C
  Canonical SMILES CCC=CCCOC(=O)CC(C)C
  External Links PubChem ID 5367681
CAS ID 35154-45-1

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Nepeta nuda
  Factor Name: Locality Variation; Developmental Stage Variation [1]
              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: Pre-blooming stage + (Locality: Suva planina, east of Serbia, Yugoslavia)
 Aerial parts Yugoslavia
NP Content: 0.9 %
 
Aerial part: Blooming stage + (Locality: Durmito, Montenegro, Yugoslavia)
 Aerial parts Yugoslavia
NP Content: 0.1 %
 
Aerial part: Blooming stage + (Locality: Suva planina, east of Serbia, Yugoslavia)
 Aerial parts Yugoslavia
NP Content: 0.1 %
      Species Name: Teucrium chamaedrys
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. chamaedrys were collected at the flowering stage in June 2004 near Corti, Corsica, France and near Oristano, Sardinia, Italy
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               Factor Function
The Corsican and Sardinian oils of T. chamaedrys investigated in this study were qualitatively similar but they differed by the amount of their major components. The major components were beta-caryophyllene (29.0% and 27.4%, respectively) and germacrene D (19.4% and 13.5%, respectively), followed by alpha-humulene (6.8%) and delta-cadinene (5.4%) in the Corsican oil and by caryophyllene oxide (12.3%) and alpha-humulene (6.5%) in the Sardinian oil. These quantitative differences are also noticeable on the amounts of the different class compounds. Especially, the monoterpene hydrocarbons amounted for 10.3% and 4.1% in Sardinian and Corsican oils respectively and the oxygenated sesquiterpenes amounted for 18.9% and only 7.4% in both oils, respectively. Both oils were qualitatively rather similar in comparison with those reported in the literature from various geographic regions. However, among the 87 components identified in this study, 47 minor components (< 0.6%) reported were identified for the first time in T. chamaedrys oil. This study confirms the quantitative variability of the major components according to the plant origin.
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               Factor Part Location NP Content
 
Locality: Corti, Corsica, France
 Aerial parts France
NP Content: <0.05 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [3]
              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 Quantity and Composition of Essential Oil of the Wild Plant Nepeta nuda L. from Yugoslavia
2 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia
3 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey