General Information of Natural Product (ID: NP0020)
  Natural Product Name
Farnesol
  Synonyms
farnesol; trans,trans-Farnesol; 106-28-5; (E,E)-Farnesol; (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol; 4602-84-0; trans-Farnesol; (2E,6E)-Farnesol; 2-trans,6-trans-Farnesol; All-trans-Farnesol; Farnesyl alcohol; 3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol; FCI 119a; Inhibitor A2; (E)-farnesol; HSDB 445; 2,6-Di-trans-Farnesol; 2,6,10-dodecatrien-1-ol, 3,7,11-trimethyl-, (2E,6E)-; (2-trans,6-trans)-farnesol; 2E,6E-farnesol; Farnesol (mixture of isomers); UNII-X23PI60R17; 3,7,11-Trimethyl-2,6,10-dodecatrienol; 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-; Farnesol, mixture of isomers; Floral Green; CHEBI:16619; 3,7,11-trimethyldodeca-2,6,10-trien-1-ol; X23PI60R17; (2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol; 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)-; Farnesol 97+% FCC; (E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol; trans,trans-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol; MFCD00002918; FEMA No. 2478; Trimethyl dodecatrienol; EINECS 225-004-1; NSC 60597; EPA Pesticide Chemical Code 128911; polyprenols; transfarnesol; Nikkosome; trans- farnesol; AI3-44561; .beta.-Farnesol; E,E-farnesol; all-trans farnesol; (E,E)farnesol; FOF; trans,trans farnesol; Farnesol (6CI); (E,E,)-farnesol; Farnesol, 95%; (2Z,6Z)-Farnesol; Farnesol (2E,6E); Farnesol, (E,E)-; Farnesol, trans, trans; ST072172; 2E,6E-Farnesyl alcohol; FARNESOL (TRANS); Spectrum5_002027; trans,trans-alpha-farnesol; DSSTox_CID_12389; DSSTox_RID_78934; trans,trans-Farnesol, 96%; trans,trans-Farnesol, 97%; DSSTox_GSID_32389; SCHEMBL58068; 2-trans-S-6-trans-farnesol; BSPBio_002660; Farnesol, analytical standard; CHEMBL25308; SPECTRUM1501022; DTXSID2040789; BDBM11021; CHEBI:26199; CHEBI:28600; HY-Y0248A; AMY33538; BCP22704; ZINC1532860; Tox21_302034; AC-422; BBL027412; CCG-38862; s4941; STL372743; AKOS004907430; LMPR0103010001; NCGC00095654-01; NCGC00095654-02; NCGC00095654-03; NCGC00095654-04; NCGC00095654-05; NCGC00255293-01; trans,trans-Farnesol, analytical standard; AS-16107; LS-14447; S409; CAS-4602-84-0; CS-0031456; T0608; 06F285; C01126; Farnesol, mixture of isomers, analytical standard; A801411; Q420449; Q-201851; W-109985; BRD-K24656285-001-01-0; Farnesol, mixture of isomers, >=95%, stabilized, FG; (2E, 6E)-3,7,11-trimethyl2,6,10-dodecatrien-1-ol; (E,E,)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol; F1905-7040; (2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trien-1-ol; Farnesol mixture of isomers stabilized with alpha tocopherol; UNII-EB41QIU6JL component CRDAMVZIKSXKFV-YFVJMOTDSA-N; 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl- (8CI,9CI); A2865747-EC66-4B9C-A593-0A066A438904; (2-trans,6-trans)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
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  Formula C15H26O
  Weight 222.37
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+
  InChI Key CRDAMVZIKSXKFV-YFVJMOTDSA-N
  Isomeric SMILES CC(=CCC/C(=C/CC/C(=C/CO)/C)/C)C
  Canonical SMILES CC(=CCCC(=CCCC(=CCO)C)C)C
  External Links PubChem ID 445070
CAS ID 106-28-5
NPASS ID NPC103213
HIT ID C0072
CHEMBL ID CHEMBL25308
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia nilagirica var. Septentrionalis
  Factor Name: Altitude Variation [1]
              Species Info Factor Info
               Experiment Detail
Leaves from mature plants of Artemisia nilagirica var. septentrionalis, before flowering, were collected from different altitudes in Himachal Pradesh such as Shimla (2210 m), Mandi (1044 m) and Manali (2050 m) in June 2005.
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               Factor Function
The major constituents of the oil show variation with changes in altitude. At lower, middle and higher altitudes, the major constituents of the oil were caryophyllene oxide (28.6%), borneol (35.8%) and camphor (46.9%), respectively. The percentages of alpha-humulene and trans-beta-guaiene also increased, but the percentage of sabinene, trans-sabinene hydrate, 4-terpineol, caryophyllene oxide and humulene epoxide-II decreased with an increase in altitude. The characteristic compounds observed in the plants from lower altitudes were 2-hexene-1-ol, beta-thujone, thujanol, myrtenol and linalyl acetate, while the higher altitude plants were characterized by the presence of alpha-pinene, beta-pinene, limonene, linalool, gamma-gurijunene, germacrene-D and farnesol.
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               Factor Part Location NP Content
 
Locality: Shimla, Himachal Pradesh, India; Altitude 2210 m
Leaves Himachal Pradesh, India
NP Content: 0.7 %
      Species Name: Cymbopogon winterianus
  Factor Name: Pest Infestation [2]
              Species Info Factor Info
               Experiment Detail
General plantation of citronella cv. Java 2 was maintained following recommended agricultural practices at the Experimental Farm of Central Institute of Medicinal and Aromatic Plants, Field Station, Hyderabad, India. The experimental station has a semi-arid tropical climate. The experiment was conducted in the same plantation for 2 consecutive years during the summer month of June 1996 and 1997, when the incidence of the disease was higher. In each year, 12 each of healthy and diseased plants were selected at random and harvested. The occurrence of the disease is generally observed during the hot summer season months, when the temperatures are in the range 36-43 ℃. Initial symptoms of the pest attack appear as yellow specks or blotches, mostly along leaf margins, that in later stages develop into yellow streaks running along the length of the affected leaves. Emerging young leaves are pale green to yellow coloured, twisted, crinkled, developed into whip-like structures and in severe cases of infection fail to open. Even if they do open, these leaves fail to exhibit a smooth leaf surface. Severely affected older leaves turn brown, dry and die. The overall growth and development of the infected plant is severely affected, giving it a dwarfed and unhealthy appearance.
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               Factor Function
The essential oil examined by GC and GC-MS from cultivated healthy plants contained citronellal (28.4%), geraniol (24.8%), citronellol (11.8%) and elemol (10.2%). The major components from diseased plants were geraniol (19.0-25.5%), elemol (15.3-20.4%), citronellal (13.4-19.1%) and citronellol (12.9-15.1%). Caryophyllene oxide (3.5-6.0%) was an important minor component.
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               Factor Part Location NP Content
 
Healthy leaves of healthy plant
Leaves Hyderabad, India
NP Content: 1 %
 
Healthy leaves of diseased plant (Yellowing and crinkling disease)
Leaves Hyderabad, India
NP Content: 1 %
 
Crinkled, whip like leaves of diseased plant (Yellowing and crinkling disease)
Leaves Hyderabad, India
NP Content: 1.3 %
 
Dead leaves of diseased plant (Yellowing and crinkling disease)
Leaves Hyderabad, India
NP Content: 1.4 %
 
Semi-diseased leaves of diseased plant (Yellowing and crinkling disease)
Leaves Hyderabad, India
NP Content: 1.1 %
      Species Name: Ducrosia assadii
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
The aerial parts of D. assadii Alava. were collected in the wild from Lalehzar (Kerman Province, in southern Iran) at the flowering stage, in July 2007. The material was dried at room temperature and used for distillation. Distillation: A direct-fired field distillation unit containing a distillation tank (capacity: 1,000 L), a condensation column and receiver, all made of stainless steel, and which can process 30-50 kg of dried aerial parts from the plants/batch, was installed at an altitude of 2600 m (boiling point: 87 ℃). Dried aerial parts from the plants (40 kg) were charged into the distillation unit along with 500 L fresh water and the unit was heated by steam. The system was kept open to atmospheric pressure until the temperature reached to 70 ℃, when the air present in the unit was replaced by the vapor. After complete removal of air from the unit, the air vent was closed and the whole unit was operated as a closed system under pressure to distill the oil. The pressure, temperature and rate of distillation were controlled manually. The process was completed after the collection of 500 L of water distillate. The oil collected in the receiver and dried over anhydrous Na2SO4. Extraction of Ducrosia Second Oil From Ducrosia Water by Redistillation: The seprated distillate water collected in the receiver was redistilled in a 1,000 L still to yield more Doucrosia oil (this oil is known as secondary essential oil, second oil, cooked oil or indirect oil).
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               Factor Function
Fifty components were identified in a second oil of D. assadii from Lalehzar with decanal (35.2%), nonadecane (12%) and citronellyl acetate (11.6%) as the main constituents. The oil from Dehbakrii also contained decanal (36.4%) as the main component of an oil recovered from the distillate water. The results showed that the amount of decanal is remarkably high in the oils of D. assadii.
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               Factor Part Location NP Content
 
Locality: Lalehzar, Kerman Province, southern Iran
Aerial parts Iran
NP Content: 0.1 %
      Species Name: Melaleuca quinquenervia (Cav.) S.T. Blake
  Factor Name: Chemotype Comparison [4]
              Species Info Factor Info
               Experiment Detail
One hundred grams of mature leaves were collected from 2 to 10 widely spaced trees per site and sent to Sydney for analysis as soon as possible after collection. Samples usually arrived in the laboratory within 48 h of collection. The majority of the sampling was done between December 1998 and October 1999. Seasonal trends in oil yields and composition are confounded in the data on geographic variation, but these were considered minor in the context of this study.
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               Factor Function
Chemotype 1 is comprised of E-nerolidol (74-95%) and linalool (14-30%) and is found from Sydney, north along the east coast of Australia to Selection Flat, New South Wales, with an isolated occurrence near Maryborough, Queensland. Two divisions occur in this chemotype which are based on the presence or absence of significant proportions of linalool (14-40%). Chemotype 2 contains 1,8-cineole (10-75%), viridiflorol (13-66%), alpha-terpineol (0.5-14%) and beta-caryophyllene (0.5-28%) in varying proportions and order of dominance in the oils. It is found throughout the distribution of the species, from Sydney to Papua New Guinea and New Caledonia. Within chemotype 2 there appears to be a continuous spread of oil composition without formation of any further discrete divisions as in chemotype 1. Analyses have shown that M. quinquenervia trees that occur at latitudes south of 25d S have high oil yields (1-3% w/w%, fresh leaves) and comprise chemotypes 1 and 2. North of 25d S, however, chemotype 1 does not occur and oil yields amongst the Australian populations are uniformly low (0.1-0.2%).
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               Factor Part Location NP Content
 
Chemotype (E-nerolidol in large concentration type)
Leaves Australia and Papua New Guinea
NP Content: 0.6 %
      Species Name: Rosa damascena
  Factor Name: Variety Comparison [5]
              Species Info Factor Info
               Experiment Detail
Experimental site: The present study was conducted at the experimental farm of the CSIR-Institute of Himalayan Bioresource Technology, Palampur (1325 m amsl, 32° 06′ 05″ N, 76° 34′10″ E), India, in 2011. Minimum temperature ranges from 3.5 ℃ to 19.8 ℃, maximum temperature ranges from 15.2 ℃ to 31.4 ℃, relative humidity varies between 62.2% and 94.1% in the morning and 45.0% and 87.2% in the evening, and bright sunshine hour ranges from 2.9 to 8.9 hours. Plant material: A population of approximately 50,000 plants raised from mixed stem cuttings collected from perennial rose plantations at the University of Agriculture, Udaipur, Rajasthan, India, and maintained in the field of the CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh, India, were utilized as an original gene pool of R. damascena. Two varieties, Jwala and Himroz were diversified through selections of desirable traits (morphological/oil content) across 25,000 plants. The five elites, three of R. damascena var. Jwala, (Indica, Super jwala and Jwala) and two of R. damascena var. Himroz (Hot himroz and Himroz) were developed through field selections and maintained at the Natural Plant Products Division Experimental Farm of the Institute. Rosa bourboniana plants were collected from the Fragrance and Flavour Development Centre, Kannauj, UP, India, during 1992 and maintained at the Natural Plant Products Division Experimental Farm of the Institute.
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               Factor Function
The essential oil content of the varieties of R. damascena varied from 0.037% to 0.051% and that of R. bourboniana was 0.017%. Super jwala recorded the highest oil content (0.051%). A total of 32 components were identified in the different varieties of rose oil. These components constituted 78.1-93.5% of the total rose oil species. The main components of rose oil were citronellol + nerol (16.3-30.1%), geraniol (15.8-29.3%), linalool (0.7-1.9%), rose oxide (0.9-2.6%), phenyl ethyl alcohol (0.1-0.4%), eugenol (0.3-2.2%), nonadecane (7.3-14.7%). The content of citronellol + nerol (30.1%) and geraniol (29.3%) was the highest in Himroz compared with other varieties.
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               Factor Part Location NP Content
 
Rosa damascena var. Himroz
Flowers India
NP Content: 0.7 %
 
Rosa damascena var. Hot Himroz
Flowers India
NP Content: 1.7 %
 
Rosa damascena var. Indica
Flowers India
NP Content: 0.5 %
 
Rosa damascena var. Jwala
Flowers India
NP Content: 1.1 %
 
Rosa damascena var. Super Jwala
Flowers India
NP Content: 1.3 %
      Species Name: Tanacetum dolichophyllum
  Factor Name: Altitude Variation [6]
              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: Tungnath; Altitude 3800m
Aerial parts Himalyas, Uttarakhand, India
NP Content: 0.6 %
      Species Name: Tanacetum larvatum
  Factor Name: Altitude Variation [7]
              Species Info Factor Info
               Experiment Detail
Aerial parts of T. larvatum were collected in July 2002, during the period of full flowering from two locations in Montenegro: Mt. Komovi (Sample I) and Mt. Prokletije (Sample II), altitude ca. 1900 m.
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               Factor Function
About 40 compounds were identified, representing ~89% and 96% of the total oil content in the Samples I and II, respectively. trans-Sabinyl acetate was found to be the dominant component (51.2% and 69.7%). Among the rest of compounds beta-pinene (7.7% and 4.3%) and camphor (6.3% and 4.3%) were the most abundant in both samples.
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               Factor Part Location NP Content
 
Locality: Mt. Komovi, Montenegro, Serbia; Altitude 1900 m
Aerial parts Serbia
NP Content: <0.1 %
References
1 Oil Constituents of Artemisia nilagirica var. septentrionalis Growing at Different Altitudes
2 Yellowing and crinkling disease and its impact on the yield and composition of the essential oil of citronella (Cymbopogon winterianus Jowitt.)
3 Chemical Composition of the Essential Oil of Ducrosia assadii Alava. from Kerman Province in Iran
4 Chemical variation in the leaf essential oil of Melaleuca quinquenervia (Cav.) S.T. Blake
5 Evaluation of several Rosa damascena varieties and Rosa bourboniana accession for essential oil content and composition in western Himalayas
6 Variation in the Constituents of Tanacetum dolichophyllum (Kitam.) Kitam. from Different Locations of Uttarakhand Himalaya (India)
7 Chemical Composition of Tanacetum larvatum Essential Oil