Details of Natural Product (NP)

General Information of Natural Product (ID: NP0013)
  Natural Product Name
Citronellyl Acetate
  Synonyms
Citronellyl acetate; 150-84-5; Citronellol acetate; 3,7-Dimethyloct-6-en-1-yl acetate; 3,7-Dimethyl-6-octen-1-yl acetate; 3,7-dimethyloct-6-enyl acetate; 1-Acetoxy-3,7-dimethyloct-6-ene; Acetic acid, citronellyl ester; Natural rhodinol, acetylated; 6-Octen-1-ol, 3,7-dimethyl-, acetate; 6-Octen-1-ol, 3,7-dimethyl-, 1-acetate; 3,7-Dimethyl-6-octen-1-ol acetate; 2-Octen-8-ol, 2,6-dimethyl-, acetate; NSC 4893; Acetic acid, 3,7-dimethyl-6-octen-1-yl ester; 3,7-Dimethyl-6-octen-1-yl ethanoate; CHEBI:70478; beta-citronellol acetate; beta-Citronellyl acetate; .beta.-Citronellyl acetate; 6-Octen-l-ol, 3,7-dimethyl-, acetate; Citronellyl ethanoate; b-citronellyl acetate; Ctronellyl acetate (natural); FEMA No. 2311; FEMA No. 2981; EINECS 205-775-0; EINECS 266-837-0; 6-Octen-1-ol, 3,7-dimethyl-, 1-acetate, (3S)-; BRN 1723886; Cephreine; Cephrol acetate; AI3-02039; Citronellylacetate; Citronellyl Extra; CitronellyI acetate; MFCD00015039; (1)-3,7-Dimethyloct-6-enyl acetate; DL-Citronellol acetate; Acetic acid citronellyl; EC 205-775-0; (+/-)-Citronellyl acetate; .beta.-Citronellol, acetate; 1-02-00-00065 (Beilstein Handbook Reference); CITRONELLYL ACETATE BRI; SCHEMBL157075; CHEMBL1453648; DTXSID5051739; 3,7-Dimethyl-6-octenyl acetate; FEMA 2311; HY-N7144A; NSC4893; WLN: 1Y1&U3Y1&WOV1; 3,7-dimethyl-6-octen-1yl acetate; NSC-4893; 7556AA; BDBM50037054; s5827; 2-Octen-8-ol,6-dimethyl-, acetate; 6-Octen-1-ol,7-dimethyl-, acetate; AKOS015899521; LMPR0102010015; MCULE-2538735041; Citronellyl acetate, analytical standard; Citronellyl acetate, >=95%, FCC, FG; NCGC00095623-01; 67650-82-2; AS-63841; acetic acid 3,7-dimethyl-6-octenyl ester; Acetic acid,7-dimethyl-6-octen-1-yl ester; DB-043064; CS-0099257; FT-0623967; D89326; A884131; Q-200868; Q27138814; 3,7-Dimethyl-6-octen-1-yl acetate;Citronellyl acetate; Citronellyl acetate, mixture of isomers, natural, >=95%, FG
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  Formula C12H22O2
  Weight 198.3
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3
  InChI Key JOZKFWLRHCDGJA-UHFFFAOYSA-N
  Isomeric SMILES CC(CCC=C(C)C)CCOC(=O)C
  Canonical SMILES CC(CCC=C(C)C)CCOC(=O)C
  External Links PubChem ID 9017
CAS ID 150-84-5
NPASS ID NPC289388
CHEMBL ID CHEMBL1453648
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Angelica glauca
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
Angelica glauca roots were collected from Himachal Pradesh and Kashmir at various locations during the year 1999-2000.
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               Factor Function
Terpene hydrocarbons (methyl octene, limonene, beta-phellendrene, beta-pinene), phthalides [(Z)-3-butyli-dene phthalide (Z)- and (E)-ligustilide] and citronellyl acetate showed large quantitative variations of different geographical locations.
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               Factor Part Location NP Content
 
Locality: Himachal Pradesh, India
 Roots Himachal Pradesh, India
NP Content: 3.4 %
 
Locality: Kashmir, India
 Roots Kashmir, India
NP Content: 10.3 %
      Species Name: Bupleurum gibraltarium
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Plant material: Samples of B. gibraltarium were gathered in November 1995 during the fruiting period (F), in May 1996 during the pre-flowering period (PF), in July 1996 during the full flowering period (FF), and in September 1996 during the late flowering period (LF) from El Zumbel area (UTM: 30SVG3278) . Every sample consisted in the whole aerial parts of five single plants growing wild near one to another. Once the plants reached the laboratory, they were airdried for seven to 15 days, and separated by parts, i.e., leaves, stems, umbel rays and, when present, fruits.
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               Factor Function
In the leaf oils, sabinene (12.0-33.9%) and limonene (7.8-23.4%) were the main components, the sabinene level being minimum in full flowering and maximum in fruiting. In stem oils, sabinene (4.7-21.6%) and 2,3,4-trimethylbenzaldehyde (9.3-13.6%) were the main components, the sabinene level being minimum in pre-flowering and maximum in full flowering. In umbel ray oils, sabinene (20.7-43.1%) was the first component in all the phenological periods, followed by alpha-pinene (7.3-28.2%). Both monoterpenes increased their levels in late flowering and reached minimum amounts in fruiting.
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               Factor Part Location NP Content
 
Leaf: full pre-flowering stage
 Leaves Spain
NP Content: 1.2 %
 
Stem: full pre-flowering stage
 Stems Spain
NP Content: 0.8 %
 
Aerial part: full flowering stage
 Aerial parts Spain
NP Content: 1.6 %
 
Umbel: full flowering stage
 Umbels Spain
NP Content: 0.7 %
      Species Name: Cymbopogon winterianus
  Factor Name: Pest Infestation [3]
              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: 3.2 %
 
Healthy leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 2.7 %
 
Crinkled, whip like leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 3 %
 
Dead leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 2.4 %
 
Semi-diseased leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 2.6 %
      Species Name: Micromeria biflora
  Factor Name: Seasonal Variation [4]
              Species Info Factor Info
               Experiment Detail
The aerial parts of M. biflora collected during November 1993 and June 1994 were used for the investigation.
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               Factor Function
The major constituents of the oil were neral (25.3-32.2%) and geranial (26.7-41.3%). The oil produced in the winter was found to contain higher amounts of oxygenated monoterpenes than the oil produced in the summer.
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               Factor Part Location NP Content
 
Harvesting time: Summer
 Aerial parts South India
NP Content: 0.57 %
 
Harvesting time: Winter
Aerial parts South India
NP Content: 0.49 %
      Species Name: Pelargonium graveolens L'Her.
  Factor Name: Cultivar Comparison; Seasonal Variation [5]
              Species Info Factor Info
               Experiment Detail
One-month-old rooted stem cuttings of three rosescented geranium cultivars, namely Bourbon type, CIM-Pawan and Kelkar were transplanted at 50 × 50 cm plant spacing in the experimental field of Central Institute of Medicinal and Aromatic Plants, Research Center Purara, Uttarakhand, in October 2007. Plants were irrigated immediately after transplanting and further crops were raised following the normal agricultural practices needed to grow the plant. The experimental site is located between the coordinates 28° 60′ and 31° 29′ N, 77° 49′ and 80° 60 m E, and at an altitude of 1250 m in the Kattyur valley. Climatologically, it is categorized as a sub-temperate (1200-1700 m) zone, where monsoon usually breaks in June and continues up to September. Sampling of the rose-scented geranium cultivars was started from March 2008 and taken on the tenth of every month until February 2009. Samples were collected in triplicate in each season. (A, cv. Bourbon type; B, cv. CIM-Pawan; C, cv. Kelkar; I, spring season; II, summer season; III, rainy season;IV, autumn season; V, winter season).
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               Factor Function
The major components in the essential oil of cv. Bourbon type were geraniol (14.1-34.6%), citronellol (15.2-31.3%), linalool (2.9-9.2%), citronellyl formate (4.4-9.2%), isomenthone (4.5-6.6%), 10-epi-gamma-eudesmol (4.7-6.7%) and geranyl formate (3.8-6.2%). The dominant constituents of the cv. CIM-Pawan essential oil were geraniol (11.9-31.9%), citronellol (16.1-30.2%), citronellyl formate (5.2-8.9%), linalool (3.7-6.4%), isomenthone (4.0-6.3%), 10-epi-gamma-eudesmol (4.4-5.2%) and geranyl formate (4.3-5.0%). However, the chemical composition and odor of cv. Kelkar was quite different from the other two cultivars and the major components found in this oil were citronellol (51.0-63.4%) and isomenthone (9.8-17.8%).
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               Factor Part Location NP Content
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: spring season)
 Fresh herb Iran
NP Content: 1.2 %
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: summer season)
 Fresh herb Iran
NP Content: 1.3 %
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: autumn season)
 Fresh herb Iran
NP Content: 1.3 %
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: winter season)
 Fresh herb Iran
NP Content: 1 %
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: rainy season)
 Fresh herb Iran
NP Content: 1.3 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: spring season)
 Fresh herb Iran
NP Content: 1.2 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: summer season)
 Fresh herb Iran
NP Content: 1.1 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: autumn season)
 Fresh herb Iran
NP Content: 1.2 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: winter season)
 Fresh herb Iran
NP Content: 1.3 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: rainy season)
 Fresh herb Iran
NP Content: 1.5 %
 
Pelargonium graveolens cv. Kelkar: (Harvesting time: spring season)
 Fresh herb Iran
NP Content: 1.3 %
 
Pelargonium graveolens cv. Kelkar: (Harvesting time: summer season)
 Fresh herb Iran
NP Content: 0.7 %
 
Pelargonium graveolens cv. Kelkar: (Harvesting time: rainy season)
 Fresh herb Iran
NP Content: 1.4 %
      Species Name: Rosa damascena
  Factor Name: Variety Comparison [6]
              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: 0.3 %
 
Rosa damascena var. Hot Himroz
 Flowers India
NP Content: 0.3 %
 
Rosa damascena var. Indica
 Flowers India
NP Content: 0.3 %
 
Rosa damascena var. Jwala
 Flowers India
NP Content: 0.3 %
 
Rosa damascena var. Super Jwala
 Flowers India
NP Content: 0.4 %
      Species Name: Thymus vulgaris
  Factor Name: Cultivar Comparison; Seasonal Variation [5]
              Species Info Factor Info
               Experiment Detail
One-month-old rooted stem cuttings of three rosescented geranium cultivars, namely Bourbon type, CIM-Pawan and Kelkar were transplanted at 50 × 50 cm plant spacing in the experimental field of Central Institute of Medicinal and Aromatic Plants, Research Center Purara, Uttarakhand, in October 2007. Plants were irrigated immediately after transplanting and further crops were raised following the normal agricultural practices needed to grow the plant. The experimental site is located between the coordinates 28° 60′ and 31° 29′ N, 77° 49′ and 80° 60 m E, and at an altitude of 1250 m in the Kattyur valley. Climatologically, it is categorized as a sub-temperate (1200-1700 m) zone, where monsoon usually breaks in June and continues up to September. Sampling of the rose-scented geranium cultivars was started from March 2008 and taken on the tenth of every month until February 2009. Samples were collected in triplicate in each season. (A, cv. Bourbon type; B, cv. CIM-Pawan; C, cv. Kelkar; I, spring season; II, summer season; III, rainy season;IV, autumn season; V, winter season).
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               Factor Function
The major components in the essential oil of cv. Bourbon type were geraniol (14.1-34.6%), citronellol (15.2-31.3%), linalool (2.9-9.2%), citronellyl formate (4.4-9.2%), isomenthone (4.5-6.6%), 10-epi-gamma-eudesmol (4.7-6.7%) and geranyl formate (3.8-6.2%). The dominant constituents of the cv. CIM-Pawan essential oil were geraniol (11.9-31.9%), citronellol (16.1-30.2%), citronellyl formate (5.2-8.9%), linalool (3.7-6.4%), isomenthone (4.0-6.3%), 10-epi-gamma-eudesmol (4.4-5.2%) and geranyl formate (4.3-5.0%). However, the chemical composition and odor of cv. Kelkar was quite different from the other two cultivars and the major components found in this oil were citronellol (51.0-63.4%) and isomenthone (9.8-17.8%).
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               Factor Part Location NP Content
 
Pelargonium graveolens cv. Kelkar: (Harvesting time: autumn season)
 Fresh herb Iran
NP Content: 1.6 %
References
1 Variability in the Essential Oil of Angelica glauca Edgew of Different Geographical Regions
2 Seasonal Variation of Leaf, Stem and Umbel Ray Essential Oils of Bupleurum gibraltarium Lam.
3 Yellowing and crinkling disease and its impact on the yield and composition of the essential oil of citronella (Cymbopogon winterianus Jowitt.)
4 Composition of the Essential Oil of Micromeria biflora
5 Essential oil composition of Pelargonium graveolens L'Her ex Ait. cultivars harvested in different seasons
6 Evaluation of several Rosa damascena varieties and Rosa bourboniana accession for essential oil content and composition in western Himalayas