General Information of Natural Product (ID: NP0370)
  Natural Product Name
Thymol Acetate
  Synonyms
Thymol acetate; Thymyl acetate; Acetylthymol; 528-79-0; Thymol, acetate; O-Acetylthymol; (5-methyl-2-propan-2-ylphenyl) acetate; Phenol, 5-methyl-2-(1-methylethyl)-, acetate; UNII-6I29126I5V; Phenol, 5-methyl-2-(1-methylethyl)-, 1-acetate; CHEBI:9583; 6I29126I5V; Acetyl thymol; EINECS 208-442-8; NSC 406522; Thymol derivative, 17; AI3-03427; SCHEMBL250091; CHEMBL3343661; DTXSID40862124; BDBM248169; HMS1728G14; ZINC899536; 2-Isopropyl-5-methylphenol acetate; NSC406522; 2-acetoxy-1-isopropyl-4-methylbenzene; 2-Isopropyl-5-methylphenyl acetate #; (2-isopropyl-5-methyl-phenyl) acetate; NSC-406522; C09909; Q27108438
Click to Show/Hide
  Formula C12H16O2
  Weight 192.25
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C12H16O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h5-8H,1-4H3
  InChI Key WFMIUXMJJBBOGJ-UHFFFAOYSA-N
  Isomeric SMILES CC1=CC(=C(C=C1)C(C)C)OC(=O)C
  Canonical SMILES CC1=CC(=C(C=C1)C(C)C)OC(=O)C
  External Links PubChem ID 68252
CAS ID 528-79-0
NPASS ID NPC280760
CHEMBL ID CHEMBL3343661
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Satureja cuneifolia
  Factor Name: Developmental Stage Variation [1]
              Species Info Factor Info
               Experiment Detail
Satureja cuneifolia Ten. growing wild in Middle Anatolian provinces of Turkey were collected at various growth stages: a =from Konya, collected in June, before flowering; b = from Konya, collected in July, from flowering plants; c =from Konya, collected in August, full-bloom plants.
Click to Show/Hide
               Factor Function
In the oils of S. cuneifolia, 38 compounds were identified, with thymol (43.6-65.5%), carvacrol (4.7-31.2%), gamma-terpinene (trace-13.7%) and p-cymene (trace-11.5%) being dominant.
Click to Show/Hide
               Factor Part Location NP Content
 
Aerial part: Before Flowering stage
Aerial parts Middle Anatolia, Turkey
NP Content: 0.4 %
 
Aerial part: Full Blooming stage
Aerial parts Middle Anatolia, Turkey
NP Content: 0.6 %
 
Aerial part: Flowering stage
Aerial parts Middle Anatolia, Turkey
NP Content: 0.2 %
      Species Name: Satureja hortensis
  Factor Name: Drought Stress Treatment; Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Seeds of Iranian native savory were obtained from the seed bank of the Research Institute of Forests and Rangelands, Tehran, Iran, and were sown in the field on 30 March 2000. Plants were 0.2 m apart with 0.5 m between rows. For the water stress study, each plot, four rows wide and 10 m long, with four replications in a randomized complete block design, was irrigated regularly with furrow irrigation. The timing of irrigation (frequency and duration) was based on the soil water potential, according to treatment criteria. Soil water potential was monitored using sensors and leaf water potential was measured using a pressure chamber. Five irrigation treatments were determined, consisting of: (a) a control, which was irrigated to full field capacity (FC) during the growing season; (b) two moderate water stress treatments (66% of FC) during vegetative and flowering stages; and (c) two severe water stress treatments during the vegetative and flowering stages (33% of FC). Because the severe treatment during the vegetative stage resulted in stopping of plant growth and adaptation, this treatment was omitted from our studies. For each treatment, measurements of plant height and fresh and dry weight were monitored by destructive harvests of eight randomly selected plants from the centre rows of each plot during the full flowering period. Plants were harvested at the soil surface, immediately weighed (fresh weight) and then oven-dried at 75 ℃ for 48 h and reweighed (dry weight). Also, for essential oil contents, the aerial parts of eight selected plants were collected and air-dried in the shade for 24 h and then were evaluated. All essential oil concentrations reported are based on the harvest of all aerial parts from whole plants.
Click to Show/Hide
               Factor Function
The accumulation of oil increased significantly under severe water stress at the flowering stage, when the mean leaf water potential decreased from -0.5 to -1.6 MPa. This treatment affected the quantity of the essential oils more than moderate water stress during the vegetative and flowering stages. The main oil constituents are carvacrol and gamma-terpinene. The amount of carvacrol increased under moderate stress, while gamma-terpinene content decreased under moderate and severe water stress treatments.
Click to Show/Hide
               Factor Part Location NP Content
 
Control: Irrigated to full field capacity during the growing season
Aerial parts Iran
NP Content: 1.7 %
 
Low stress (LS1): 66% of field capacity during vegetative stages
Aerial parts Iran
NP Content: 0.8 %
 
Low stress (LS2): 66% of field capacity during flowering stages
Aerial parts Iran
NP Content: 0.7 %
 
Severe stress (HS): 33% of field capacity during flowering stages
Aerial parts Iran
NP Content: 1.2 %
      Species Name: Satureja parnassica ssp. parnassica
  Factor Name: Month Variation; Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
Fresh plant materials were obtained in 2004 and 2005. S. thymbra 1(vegetative stage: just before flowering, date: June 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 2(vegetative stage: full flowering, date: July 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 3(vegetative stage: after flowering, date: Aug 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 4(vegetative stage: fruiting, date: Sept 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 5(vegetative stage: fruiting, date: Nov 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 6(vegetative stage: fruiting, date: Feb 7, 2005, location: Mt. Immitos, altitude(m): 350); S. thymbra 7(vegetative stage: before flowering, date: May 7, 2005, location: Mt. Immitos, altitude(m): 350); S. parnassica 8(vegetative stage: before flowering, date: June 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 9(vegetative stage: just before flowering, date: July 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 10(vegetative stage: full flowering, date: Aug 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 11(vegetative stage: after flowering, date: Sept 16, 2004, location: Mt. Parnon, altitude(m): 1800).
Click to Show/Hide
               Factor Function
It is evident that the phytochemical content of the essential oils for both Satureja species varied greatly, depending on the period examined, and showed large prevalence of phenolic content. It must also be pointed out that regardless of the vegetative stage of the plant collected, the sum of the two isomeric phenol monoterpenes (carvacrol and thymol) and their biosynthetic monoterpene precursors p-cymene and gamma-terpinene represented always the bulk of each essential oil (~76%). More specificallysfor both species-during their premature vegetative stage, gamma-terpinene constitutes the major component of their essential oils. The approach of the flowering period results in the simultaneous gradual diminishment of monoterpene precursors and the prevalence of their phenolic metabolites. Thus, essential oils obtained from plants collected during the 'just before their flowering' stage contain thymol as their major component, which constitutes 27.88 and 38.51% of the total oil content for S. thymbra and S. parnassica, respectively. On the other hand, during their full flowering period carvacrol prevails as the major component, accounting for 39.10% for S. thymbra and for 34.61% for S. parnassica. The end of the flowering stage delineates a sharp decrease of carvacrol levels and the predominance of thymol as the major component of the essential oils. A few months later, as the premature vegetative stage approached, the level of gamma-terpinene was restored. The content of p-cymenesthe other major monoterpene precursor-fluctuated seasonally in a manner similar to that shown by gamma-terpinene. Other monoterpene hydrocarbons such as myrcene and alpha-terpinene were also detected in smaller quantities, whereas various monoterpene alcohols such as linalool, borneol, and terpin-4-ol were found mainly in the oils obtained after the flowering stage. Finally, it is notable that the oils obtained during the just before the full flowering period contain beta-caryophyllene as one of their major components.
Click to Show/Hide
               Factor Part Location NP Content
 
Harvesting time: before flowering satge; 16-June-2004
Leaves and stems Mt. Parnon, Peloponnese
NP Content: 0.32 %
 
Harvesting time: just before flowering satge; 16-June-2004
Leaves and stems Mt. Parnon, Peloponnese
NP Content: 0.36 %
      Species Name: Satureja thymbra
  Factor Name: Month Variation; Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
Fresh plant materials were obtained in 2004 and 2005. S. thymbra 1(vegetative stage: just before flowering, date: June 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 2(vegetative stage: full flowering, date: July 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 3(vegetative stage: after flowering, date: Aug 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 4(vegetative stage: fruiting, date: Sept 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 5(vegetative stage: fruiting, date: Nov 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 6(vegetative stage: fruiting, date: Feb 7, 2005, location: Mt. Immitos, altitude(m): 350); S. thymbra 7(vegetative stage: before flowering, date: May 7, 2005, location: Mt. Immitos, altitude(m): 350); S. parnassica 8(vegetative stage: before flowering, date: June 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 9(vegetative stage: just before flowering, date: July 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 10(vegetative stage: full flowering, date: Aug 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 11(vegetative stage: after flowering, date: Sept 16, 2004, location: Mt. Parnon, altitude(m): 1800).
Click to Show/Hide
               Factor Function
It is evident that the phytochemical content of the essential oils for both Satureja species varied greatly, depending on the period examined, and showed large prevalence of phenolic content. It must also be pointed out that regardless of the vegetative stage of the plant collected, the sum of the two isomeric phenol monoterpenes (carvacrol and thymol) and their biosynthetic monoterpene precursors p-cymene and gamma-terpinene represented always the bulk of each essential oil (~76%). More specificallysfor both species-during their premature vegetative stage, gamma-terpinene constitutes the major component of their essential oils. The approach of the flowering period results in the simultaneous gradual diminishment of monoterpene precursors and the prevalence of their phenolic metabolites. Thus, essential oils obtained from plants collected during the 'just before their flowering' stage contain thymol as their major component, which constitutes 27.88 and 38.51% of the total oil content for S. thymbra and S. parnassica, respectively. On the other hand, during their full flowering period carvacrol prevails as the major component, accounting for 39.10% for S. thymbra and for 34.61% for S. parnassica. The end of the flowering stage delineates a sharp decrease of carvacrol levels and the predominance of thymol as the major component of the essential oils. A few months later, as the premature vegetative stage approached, the level of gamma-terpinene was restored. The content of p-cymenesthe other major monoterpene precursor-fluctuated seasonally in a manner similar to that shown by gamma-terpinene. Other monoterpene hydrocarbons such as myrcene and alpha-terpinene were also detected in smaller quantities, whereas various monoterpene alcohols such as linalool, borneol, and terpin-4-ol were found mainly in the oils obtained after the flowering stage. Finally, it is notable that the oils obtained during the just before the full flowering period contain beta-caryophyllene as one of their major components.
Click to Show/Hide
               Factor Part Location NP Content
 
Harvesting time: just before flowering satge; 7-June-2004
Leaves and stems Mt. Immitos, Continental Greece
NP Content: 0.32 %
 
Harvesting time: full flowering satge; 7-June-2004
Leaves, stems and flowers Mt. Immitos, Continental Greece
NP Content: 0.08 %
 
Harvesting time: after flowering satge; 7-August-2004
Leaves, stems and flowers Mt. Immitos, Continental Greece
NP Content: <0.05 %
 
Harvesting time: fruiting satge; 7-September-2004
Leaves and stems Mt. Immitos, Continental Greece
NP Content: <0.05 %
 
Harvesting time: fruiting satge; 7-November-2004
Leaves and stems Mt. Immitos, Continental Greece
NP Content: 0.44 %
 
Harvesting time: fruiting satge; 7-February- 2005
Leaves and stems Mt. Immitos, Continental Greece
NP Content: 0.31 %
 
Harvesting time: before flowering satge; 7-May-2005
Leaves and stems Mt. Immitos, Continental Greece
NP Content: 0.26 %
 
Harvesting time: full flowering satge; 16-August-2004
Leaves, stems and flowers Mt. Parnon, Peloponnese
NP Content: 0.38 %
 
Harvesting time: after flowering satge; 16-September-2004
Leaves, stems and flowers Mt. Parnon, Peloponnese
NP Content: 0.44 %
      Species Name: Thymus longicaulis
  Factor Name: Chemotype Comparison [4]
              Species Info Factor Info
               Experiment Detail
Aerial parts of the plants with distinct odors, harvested at full flowering stage, were collected from the same population (growing in an area of one m2) on Mt. Parnis Attiki, at an altitude of 1200 m in June 1995.
Click to Show/Hide
               Factor Function
Limonene (18.7%) and thymol (19.4%); geraniol (56.8%) and geranyl acetate (7.6%); linalool (63.1%) and alpha-terpinyl acetate (20.4%) were the predominant components in each of the three different chemotypes, respectively.
Click to Show/Hide
               Factor Part Location NP Content
 
Chemotype (thyme-odor type)
Aerial parts Attiki, Greece
NP Content: 0.1 %
 
Chemotype (rose-odor type)
Aerial parts Attiki, Greece
NP Content: 0.2 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities in north western Turkey. A = Trabzon: Caykara, Soganli dag on July 28, 1994; B = Bayburt: Caykara, Mohakambo yaylasi on July 25, 1994; C = Trabzon: Koprubasi, Vizara yaylasi on July 20, 1994.
Click to Show/Hide
               Factor Function
One hundred and four compounds were identified representing 97.5-99.5% of the total components detected in thymol/carvacrol (50.14/10.67%), thymol/linalool (23.14/20.24%) and linalool/alpha-terpinyl acetate/geraniol (21.55/16.70/11.17%) rich oils.
Click to Show/Hide
               Factor Part Location NP Content
 
Locality: Soganli dag, Caykara, Trabzon, Eskisehir, Turkey
Aerial parts Eskisehir, Turkey
NP Content: <0.1 %
      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
Click to Show/Hide
               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.
Click to Show/Hide
               Factor Part Location NP Content
 
Locality: Karadere, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: 0.2 %
 
Locality: Evciler Village, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: 0.1 %
References
1 Essential Oils of Four Turkish Wild-Growing Labiatae Herbs: Salvia cryptantha Montbr. et Auch., Satureja cuneifolia Ten., Thymbra spicata L. and Thymus cilicicus Boiss. et Bal.
2 The influence of water stress on plant height, herbal and essential oil yield and composition in Satureja hortensis L.
3 Characterization of the essential oil volatiles of Satureja thymbra and Satureja parnassica: influence of harvesting time and antimicrobial activity
4 Chemical Composition and Antibacterial Properties of Thymus longicaulis subsp. chaoubardii Oils: Three Chemotypes in the Same Population
5 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey
6 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey