Details of Natural Product (NP)

General Information of Natural Product (ID: NP0132)
  Natural Product Name
Perillyl Alcohol
  Synonyms
PERILLYL ALCOHOL; Perilla alcohol; 536-59-4; Isocarveol; Perillol; 1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-; 4-Isopropenylcyclohex-1-en-1-ylmethanol; Hydrocumin alcohol; p-Mentha-1,8-dien-7-ol; (4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol; 4-Isopropenyl-cyclohex-1-ene-1-methanol; Dihydrocuminyl alcohol; 4-Isopropenyl-1-cyclohexene carbinol; Iso-carveol; (4-prop-1-en-2-ylcyclohexen-1-yl)methanol; 1-Hydroxymethyl-4-isopropenyl-1-cyclohexene; 4-(1-Methylethenyl)-1-cyclohexene-1-methanol; CHEBI:15420; 1,8-p-Menthadien-7-ol; Cyclohex-1-ene-1-methanol, 4-(1-methylethenyl)-; [4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol; Para-mentha-1,8-dien-7-ol; Perillic alcohol; CHEMBL444711; FEMA No. 2664; Dihydrocuminic alcohol; Dihydroperilla alcohol; (4-(prop-1-en-2-yl)cyclohex-1-enyl)methanol; NSC 641066; EINECS 208-639-9; perill alcohol; 1-perillalcohol; CCRIS 8461; 100692-55-5; dihydrocuminyl alcoholn; l(-)-perillyl alcohol; Spectrum2_000838; Spectrum3_001974; BENCYNOATEHYDROCHLORIDE; BSPBio_003574; STERCOBILINHYDROCHLORIDE; SCHEMBL296111; SPECTRUM1505297; SPBio_000795; DTXSID4052180; KBio3_002951; HY-N7000; 4-Isopropenyl-1-cyclohexene-methanol; BDBM50252404; CCG-40267; MFCD00001567; s3853; 4-isopropenyl-cyclohex-1-enylmethanol; AKOS006227854; CS-W019441; MCULE-1420218917; SB45076; SDCCGMLS-0066882.P001; NCGC00095297-01; NCGC00095297-02; NCGC00095297-03; AC-35110; (4-Isopropenyl-1-cyclohexen-1-yl)methanol; DB-065484; DB-071728; FT-0627990; FT-0690515; A870664; SR-05000002384; SR-05000002384-1; BRD-A13323580-001-03-0; Q15391928; F9405E33-6136-4D27-A15E-C10CDC8C9AC4
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  Formula C10H16O
  Weight 152.23
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
  InChI Key NDTYTMIUWGWIMO-UHFFFAOYSA-N
  Isomeric SMILES CC(=C)C1CCC(=CC1)CO
  Canonical SMILES CC(=C)C1CCC(=CC1)CO
  External Links PubChem ID 10819
CAS ID 536-59-4
NPASS ID NPC148216
HIT ID C0087
CHEMBL ID CHEMBL444711
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia verlotiorum
  Factor Name: Developmental Stage Variation [1]
              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.
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               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.
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               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: Citrus sinensis (Hongjiang)
  Factor Name: Variety Comparison [2]
              Species Info Factor Info
               Experiment Detail
Four kinds of fresh sweet oranges were obtained in the same season, November 2000, in Guangzhou. Citrus sinensis var. Hongjiang (called 'hong jiang chen' in Chinese) and C. sinensis Osbeck var. Anliu (called 'luo gang chen') were obtained at an orchard in Luo gang in Guangzhou (25 km from the center of Guangzhou). Citrus sinensis var. Sihui (called 'sihui ju') was harvested at the Shigou Experimental Farm in Sihui City in Guangdong Province (75 km far away from Guangzhou). Citrus sinensis var. Washington navel (called 'qi chen') which was produced in Jiangxi Province (200 km from Guangzhou; bordering Guangdong Province), was purchased at the wholesale market in Guangzhou. All oranges were kept in a cold room until prepared a few days later.
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               Factor Function
The peel oil compositions of four kinds of sweet oranges in China, Citrus sinensis Osbeck var. Hongjian, C. sinensis Osbeck var. Anliu, C. sinensis Osbeck var. Sihui and C. sinensis Osbeck var. Washington navel, were investigated by GC and GC/MS. The essential oils were extracted by cold-pressing method. Forty-two to 53 compounds were quantitatively determined for each variety. Their percentages, respectively, were: > 97.3%, > 98.4%, > 97.5% and > 98.0% in hydrocarbons; > 1.5%, > 0.7%, > 0.8% and > 0.9% in total aldehydes; 0.8%, 0.5%, 0.5% and 0.5% in alcohols. Either cis-or trans-limonene oxide was detected in small amounts in each of the four samples, with Hongjiang containing both limonene oxides. delta-3-Carene was commonly quantified at a level of 0.1% in all the samples. The content of aliphatic aldehydes, including octanal, nonanal, decanal and dodecanal, exceeded that of terpene aldehydes, such as neral and geranial in Hongjiang (0.9%) and Washington navel (0.6%), whereas the aliphatic aldehydes in Anliu and Sihui were present to a lesser degree than the terpene aldehydes. Either alpha- or beta-sinensal was detected in trace amounts in each of the four samples. Linalool was the major alcohol in all the samples. Nootkatone was not detected.
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               Factor Part Location NP Content
 
Citrus sinensis var. Hongjiang
 Fruits China
NP Content: < 0.005 %
 
Citrus sinensis var. Washington navel
 Fruits China
NP Content: < 0.005 %
      Species Name: Mentha longifolia
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
Plants were collected in the Inner plain, the Sharon plain and the kava valley.
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               Factor Function
The major constituent of all three oils was found to be 1,8-cineole (26.4-34.5%) followed by menthone (10.0-16.7%), pulegone (7.0-7.5%), and isomenthone (4.7-7.8%). Despite some differences in the component proportions, the plants of all three populations clearly belong to the same chemotype.
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               Factor Part Location NP Content
 
Locality: Inner plain, Israel
 Aerial parts Israel
NP Content: trace %
      Species Name: Salvia aucheri
  Factor Name: Variety Comparison [4]
              Species Info Factor Info
               Experiment Detail
S. aucheri var. aucheri was collected in Karaman: Ermenek to Mutt Road on July 19,1995; Salvia aucheri var. canescens was collected in Karaman: Ermenek, Tekecati Valley on July 19,1995.
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               Factor Function
Eighty components were characterized in the Salvia aucheri var. aucheri oil, with camphor (21.1%), 1, 8-cineole (20.3%), borneol (7.8%), spathulenol (6.3%) and camphene (5.3%) as major constituents. 1, 8-Cineole (25.2%), camphor (17.9%), borneol (10.6%), alpha-pinene (5.4%) and camphene (5.3%) were identified as major constituents among the 88 components characterized in the oil of Salvia aucheri var. canescens.
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               Factor Part Location NP Content
 
Salvia aucheri var. aucheri
 Aerial parts Karaman, Turkey
NP Content: 0.1 %
 
Salvia aucheri var. canescens
 Aerial parts Karaman, Turkey
NP Content: <0.01 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [5]
              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.
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               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.
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               Factor Part Location NP Content
 
Salvia euphratica var. euphratica
 Flowering aerial parts Turkey
NP Content: 0.3 %
 
Salvia euphratica var. leiocalycina
 Flowering aerial parts Turkey
NP Content: 0.4 %
      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
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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: 0.2 %
 
Locality: Karadere, Kirklareli, Turkey
 Aerial parts Kirklareli, Turkey
NP Content: 0.1 %
References
1 Chemical Variation in the Oil of Artemisia verlotiorum Lamotte of French Origin Harvested at a Vegetative Stage and During Flowering
2 Volatile Constituents of the Peel Oils of Several Sweet Oranges in China
3 Volatile Extract of Mentha longifolia Growing in Israel. Aromatic Plants of the Holy Land and the Sinai. Part XIII
4 Composition of Essential Oils from Two Varieties of Salvia aucheri Benth. Growing in Turkey
5 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
6 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey