Details of Natural Product (NP)

General Information of Natural Product (ID: NP0236)
  Natural Product Name
1-Hexanol
  Synonyms
1-Hexanol; Hexan-1-ol; Hexyl alcohol; 111-27-3; HEXANOL; n-Hexanol; n-Hexyl alcohol; Amylcarbinol; 1-Hexyl alcohol; 1-Hydroxyhexane; Caproyl alcohol; Pentylcarbinol; Caproic alcohol; n-Hexan-1-ol; C6 alcohol; Alcohol(C6); Hexanol (VAN); Fatty alcohol(C6); EPAL 6; Hexyl alcohol (natural); Alcohol C-6; UNII-6CP2QER8GS; NSC 9254; MFCD00002982; Hexanol-(1); 6CP2QER8GS; 25917-35-5; CHEBI:87393; DSSTox_CID_1931; DSSTox_RID_76410; DSSTox_GSID_21931; Caswell No. 482E; Hydroxyhexane; Hexanols; FEMA Number 2567; CAS-111-27-3; HE2; FEMA No. 2567; HSDB 565; EINECS 203-852-3; EPA Pesticide Chemical Code 079047; BRN 0969167; Caproalcohol; Hexalcohol; HEXYL ALCOHOL, ACTIVE; n-hexylalcohol; AI3-08157; N-hexenol; Nat.Hexanol; Exxal 6; EINECS 247-346-0; Alcohols, C6-9; HEXANOL-CMPD; Exxal 6 (Salt/Mix); BDBM9; 1-Hexanol, 98%; Hexyl alcohol, FCC, FG; EC 203-852-3; n-C6H13OH; SCHEMBL1877; NATURAL HEXYL ALCOHOL; C6H13OH; WLN: Q6; 4-01-00-01694 (Beilstein Handbook Reference); MLS001055374; UN 2282 (Salt/Mix); BIDD:ER0298; CHEMBL14085; 1-Hexanol, analytical standard; DTXSID8021931; 1-Hexanol, anhydrous, >=99%; NSC9254; 1-Hexanol, reagent grade, 98%; DTXSID001022586; HMS3039L08; BCP29486; NSC-9254; ZINC1699882; Tox21_201335; Tox21_302953; LMFA05000117; STL282713; UN2282; AKOS009031422; HY-W032022; MCULE-4299150163; Alcohol C-6, Natural, Natural Hexanol; 1-Hexanol, purum, >=98.0% (GC); 1-Hexyl alcohol pound>>1-Hexylalcohol; NCGC00090949-01; NCGC00090949-02; NCGC00256385-01; NCGC00258887-01; Hexanols [UN2282] [Flammable liquid]; LS-13216; SMR000677945; 1-Hexanol, SAJ special grade, >=99.0%; 1-Hexanol, Vetec(TM) reagent grade, 98%; CS-0076046; FT-0607887; H0130; Hexyl alcohol, natural, >=98%, FCC, FG; EN300-19338; Q76933; 1-Hexanol, ReagentPlus(R), >=99.5% (GC); J-002549; F0001-0237; Z955123546; 71076-86-3
Click to Show/Hide
  Formula C6H14O
  Weight 102.17
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3
  InChI Key ZSIAUFGUXNUGDI-UHFFFAOYSA-N
  Isomeric SMILES CCCCCCO
  Canonical SMILES CCCCCCO
  External Links PubChem ID 8103
CAS ID 111-27-3
NPASS ID NPC275462
CHEMBL ID CHEMBL14085
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Arabidopsis thaliana
  Factor Name: T-DNA Knock-Out Treatment [1]
              Species Info Factor Info
               Experiment Detail
In vitro cultivation of Arabidopsis wildtype and mutant plants: Seeds were sterilized according to standard lab routines (EtOH, NaOCl/NaOH) prior to aseptical (in vitro) cultivation in 500 ml screw cap jars on MS medium (4.3 g/l; 50 ml/jar) containing Bacto- and Phytoagar (1:2; 6 g/l) and 30 g/l sucrose. Ten seeds were pipetted into each jar and plants grown for 6 weeks until flowering at a temperature of 20 ℃ under a 16/8 h day/ night regime using fluorescent tubes (Osram Lumilux Plus Eco 36 W). Both Arabidopsis thaliana wildtype plants of ecotype Columbia-0 (Col) and 4 Col-derived T-DNA knock-out mutants (homozygous lines) showing deficiencies in the GLS biosynthesis pathway were used in this study (five parallels for wildtype and mutants): TGG1 (Atg526000; Salk_130469), TGG2 (At5g25980; Salk_038730), Cyp83A1 (At4g13770) and Cyp83B1 (At4g31500; Salk_028573). Greenhouse-cultivation of Arabidopsis ecotypes: The following Arabidopsis ecotypes were used in the study: Columbia (Col), Cape Verde Islands (Cvi), Landsberg erecta (Ler) and Wassilewskija (Ws). Single plants were greenhouse-cultivated on fertilized soil (P-Jord; Emmaljunga Torvmull AB) in plug trays (9 × 6 cells) at a temperature of 20 ℃ (three parallels for each ecotype). Due to the 6-weeks growth period (November/December 2003), the plants were cultivated under a 16/8 h day/night regime using metal halide lamps (Osram HQI-T 400 W) placed 130 cm above the trays. Depending on the ecotypical plant development, whole plants were sampled after 3-4 weeks right before bolting for in vivo studies, while investigations of single plant organs (leaf, stem, inflorescence) were carried out after 5-6 weeks of cultivation.
Click to Show/Hide
               Factor Function
Metabolites from methionine, leucine and phenylalanine-derived glucosinolates were most abundant (4-methylthiobutyl, 4-methylpentyl, 2-phenylethyl). In addition, 24 monoterpenes, 26 sesquiterpenes and 12 aromatic structures, predominantly observed in inflorescenses, are described. Excluding the vast group of straight chain aliphatic structures, a total of 102 volatile compounds were detected, of which 59 are reported in Arabidopsis thaliana for the first time, thus emphasizing the sensitivity and applicability of solid-phase microextraction for volatile profiling of plant secondary metabolites.
Click to Show/Hide
               Factor Part Location NP Content
 
Arabidopsis thaliana wildtype
 Whole plant Norway
NP Content: 1.6 %
 
A. thaliana T-DNA knock-out mutant Cyp83A1: (At4g13770)
 Whole plant Norway
NP Content: 3.06 %
 
A. thaliana T-DNA knock-out mutant Cyp83B: (At4g31500; Salk_028573)
 Whole plant Norway
NP Content: 3.64 %
 
A. thaliana T-DNA knock-out mutant TGG1: (Atg526000; Salk_130469)
 Whole plant Norway
NP Content: 1.43 %
 
A. thaliana T-DNA knock-out mutant TGG2: (At5g25980; Salk_038730)
 Whole plant Norway
NP Content: 1.65 %
      Species Name: Artemisia absinthium
  Factor Name: Chemotype Comparison [2]
              Species Info Factor Info
               Experiment Detail
Ten different plants of wormwood were collected in March 1997 from each one of the following four wild populations in the Spanish Pyrenees: Tallo de Aulet (prov. Huesca) and Pont de Suert, Sort and Farga de Moles (prov. Lleida). In three of the four populations studied, there was another chemotype, with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate. This chemotype, called chemotype B, was less frequent in the Pyrenees than the chemotype A, appearing only in 17% of the samples (two samples in TallO de Aulet and in Pont de Suert and three samples in Farga de Moles).
Click to Show/Hide
               Factor Function
Two chemotypes were detected; a cis-epoxyocimene type (with more than 50% of this compound) which was predominant in all the populations, and a cis-epoxyocimene + chrysanthenyl acetate type (with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate). The distribution of these chemotypes had no relation with the altitude of the samples.
Click to Show/Hide
               Factor Part Location NP Content
 
Chemotype (cis-epoxyocimene type)
 Leaves Spain
NP Content: <0.03 %
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [3]
              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: 0.2 %
 
Artemisia annua cv. Jeevanraksha
 Aerial parts India
NP Content: <0.05 %
      Species Name: Artemisia verlotiorum
  Factor Name: Developmental Stage Variation [4]
              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.
Click to Show/Hide
               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.
Click to Show/Hide
               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: Fritillaria imperialis
  Factor Name: Cultivar Comparison [5]
              Species Info Factor Info
               Experiment Detail
Plants of the F. imperialis cultivars Premier (very strong foxy odor) and Lutea (strong foxy odor), the F. imperialis subspecies Inodora (no odor), a cross between F. imperialis Lutea × Inodora (F1 generation, faint foxy odor) were grown from bulbs during the spring and early summer in clay soil near Midlum (Province of Friesland, The Netherlands). Bulbs, newly grown from these plants, were harvested in mid-June and stored, after removal of soil, at ambient temperature until analysis, which occurred in October and November.
Click to Show/Hide
               Factor Function
GC-O revealed that the foxy odor was caused by a single component, identified as 3-methyl-2-butene-1-thiol on the basis of smell in GC-O analyses (two GC columns), mass spectra, and retention times. The abundance of 3-methyl-2-butene-1-thiol is consistent with the intensity of foxy Fritillaria odor in the F. imperialis cultivars: Premier > Lutea >> Lutea × Inodora, where the latter did not show a detectable peak in GC-MS.
Click to Show/Hide
               Factor Part Location NP Content
 
Fritillaria imperialis cv. Inodora (no odor)
 Flowers Netherlends
NP Content: 0.3 %
 
Fritillaria imperialis cv. Lutea × Inodora (faint foxy odor)
 Flowers Netherlends
NP Content: 1.5 %
 
Fritillaria imperialis cv. Lutea (strong foxy odor)
 Flowers Netherlends
NP Content: 1.1 %
 
Fritillaria imperialis cv. Premier (very strong foxy odor)
 Flowers Netherlends
NP Content: 3.5 %
      Species Name: Lavandula latifolia
  Factor Name: Developmental Stage Variation [6]
              Species Info Factor Info
               Experiment Detail
Plant material: Samples of L. latifolia were collected in August 1998 during the full flowering period (L/La) and in October 1998 during the fruiting period (L/Lb) from three different spike lavender populations located into the Cazorla, Segura y Las Villas Natural Park (Jaen province, Spain). The plant material from each population consisted of the twigs of several single plants. L/La (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: August 14, 1998, Phenological stage: Flowering); L/Lb (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: October 15, 1998, Phenological stage: Fruiting).
Click to Show/Hide
               Factor Function
The small amounts of linalool needed to match the standard can be reached in a natural way (from full flowering to fruiting) which means it is important to choose the most convenient time of harvest in the studied area.
Click to Show/Hide
               Factor Part Location NP Content
 
Whole plant: Flowering stage
 Whole plant Spain
NP Content: <0.1 %
 
Whole plant:Fruiting stage
 Whole plant Spain
NP Content: 0.1 %
      Species Name: Myrtus communis var. italica
  Factor Name: Month Variation [7]
              Species Info Factor Info
               Experiment Detail
Myrtle (M. communis var. italica) aerial parts were collected monthly during 2006-2007 from Jbal Stara of Haouaria region in North Tunisia, belonging to a subhumid bioclimate.
Click to Show/Hide
               Factor Function
In conclusion, high fluctuations were observed in the oil yields and composition of different parts of Myrtus communis var. italica during all the collecting periods. They could be explained by genetic and environmental factors. Moreover, significant differences were revealed in the main oil compounds. alpha-Pinene percentages showed the most remarkable changes among the different part oils. So, leaf oils contained more alpha-pinene than those of the fruits and stems during the myrtle vegetative cycle.
Click to Show/Hide
               Factor Part Location NP Content
 
Leaf: (Harvesting time: March)
 Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: May)
 Leaves Tunisia
NP Content: 0.2 %
 
Leaf: (Harvesting time: June)
 Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: July)
 Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: August)
 Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: September)
 Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: October)
 Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: November)
 Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: December)
 Leaves Tunisia
NP Content: 0.1 %
 
Fruit: (Harvesting time: September)
 Fruits Tunisia
NP Content: 0.1 %
 
Fruit: (Harvesting time: October)
 Fruits Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: January)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: February)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: March)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: April)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: May)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: June)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: July)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: August)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: September)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: October)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: November)
 Stems Tunisia
NP Content: 0.1 %
 
Stem: (Harvesting time: December)
 Stems Tunisia
NP Content: 0.1 %
      Species Name: Sideritis congesta
  Factor Name: Locality Variation [8]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities. A: Antalya: Alanya, Sapadere, Beldibi-Baskoy in July 1991 (ESSE 9562). B: Icel: Anamur, Kas yaylasi in July 1991 (ESSE 9192).
Click to Show/Hide
               Factor Function
Thirty-nine components were characterized in each oil representing 85-90% of the total components detected with beta-pinene (34-35%) and alpha-pinene (24-25%) as major constituents.
Click to Show/Hide
               Factor Part Location NP Content
 
Locality: Beldibi-Baskoy, Sapadere, Alanya, Antalya, Turkey
 Inflorescence Turkey
NP Content: <0.1 %
 
Locality: Kas yaylasi, Anamur, Icel, Turkey
 Inflorescence Turkey
NP Content: <0.1 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [9]
              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: Shahr-e-kord, western Iran
 Aerial parts Iran
NP Content: <0.05 %
      Species Name: Teucrium chamaedrys
  Factor Name: Locality Variation [10]
              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
Click to Show/Hide
               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.
Click to Show/Hide
               Factor Part Location NP Content
 
Locality: Corti, Corsica, France
 Aerial parts France
NP Content: <0.05 %
 
Locality: Oristano, Sardinia, Italy
 Aerial parts Italy
NP Content: <0.05 %
      Species Name: Vitis vinifera
  Factor Name: Variety Comparison [11]
              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.
Click to Show/Hide
               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.
Click to Show/Hide
               Factor Part Location NP Content
 
Vitis vinifera var. Cabernet Sauvignon
 Stalks Italy
NP Content: 5.72 %
 
Vitis vinifera var. Frappato
 Stalks Italy
NP Content: 0.66 %
 
Vitis vinifera var. Nerello Mascalese
 Stalks Italy
NP Content: 3.34 %
 
Vitis vinifera var. Nero d'Avola
 Stalks Italy
NP Content: 4.4 %
References
1 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
2 Essential Oil of Artemisia absinthium L. from the Spanish Pyrenees
3 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
4 Chemical Variation in the Oil of Artemisia verlotiorum Lamotte of French Origin Harvested at a Vegetative Stage and During Flowering
5 Identification of the Volatile Component(s) Causing the Characteristic Foxy Odor in Various Cultivars of Fritillaria imperialis L. (Liliaceae)
6 Chemical Composition and Seasonal Variations of Spike Lavender Oil from Southern Spain
7 Changes in Essential Oil Composition of Tunisian Myrtus communis var. italica L. During Its Vegetative Cycle
8 Composition of the Essential Oil of Sideritis congesta P.H.Davis et Hub.-Mor.
9 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
10 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia
11 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.