Details of Natural Product (NP)

General Information of Natural Product (ID: NP0269)
Natural Product Name	4-Isopropylbenzaldehyde
Synonyms	4-isopropylbenzaldehyde; cuminaldehyde; 122-03-2; cuminic aldehyde; cumaldehyde; cuminal; p-cumic aldehyde; Cumic aldehyde; Benzaldehyde, 4-(1-methylethyl)-; Cuminyl aldehyde; p-Isopropylbenzenecarboxaldehyde; P-ISOPROPYLBENZALDEHYDE; 4-(1-Methylethyl)benzaldehyde; Benzaldehyde, p-isopropyl-; 4-(Methylethyl)benzaldehyde; P-isopropyl benzaldehyde; p-Cuminic aldehyde; 4-propan-2-ylbenzaldehyde; 4-Isopropylbenzenecarboxylate; 4-(Propan-2-Yl)Benzaldehyde; 4-Isopropyl-benzaldehyde; NSC 4886; MFCD00006953; UNII-O0893NC35F; CHEMBL161577; CHEBI:28671; O0893NC35F; FEMA No. 2341; EINECS 204-516-9; BRN 0636547; Cuminadlehyde; Cuminaldehyd; Cumal; Cumin aldehyde; AI3-01853; 4-iPr-Benzaldehyde; 4isopropylbenzaldehyde; Cuminaldehyde, 98%; p-iso-Propylbenzaldehyde; p-isopropyl-Benzaldehyde; 4(isopropyl)benzaldehyde; 4-isopropyl benzaldehyde; 4-(isopropyl)benzaldehyde; DSSTox_CID_1974; p-Isopropylbenzaldehyde, f; 4(2-propyl)-benzaldehyde; bmse000508; EC 204-516-9; DSSTox_RID_76435; DSSTox_GSID_21974; SCHEMBL87226; 4-07-00-00723 (Beilstein Handbook Reference); p-(1-methylethyl)benzaldehyde; 4-Isopropylphenylcarboxaldehyde; (4-isopropyl-phenyl)-methanone; DTXSID9021974; WLN: VHR DY1 & 1; NSC4886; Cuminaldehyde, analytical standard; ZINC968248; HY-Y0790; NSC-4886; Cuminaldehyde, >=98%, FCC, FG; Tox21_300712; BDBM50139366; s5089; STL194065; AKOS000119738; AC-2430; CCG-266191; Cuminal p-(1-methylethyl)benzaldehyde; MCULE-4415970320; NCGC00248148-01; NCGC00257518-01; AS-12957; CAS-122-03-2; DB-041645; CS-0015770; FT-0624115; I0168; C06577; D70801; A804831; Q419952; W-108440; F2190-0632 Click to Show/Hide
Formula	C₁₀H₁₂O
Weight	148.2
Structure
Structure	3D Structure Download		2D Structure Download
InChI	InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3
InChI Key	WTWBUQJHJGUZCY-UHFFFAOYSA-N
Isomeric SMILES	CC(C)C1=CC=C(C=C1)C=O
Canonical SMILES	CC(C)C1=CC=C(C=C1)C=O
External Links	PubChem ID	326
	CAS ID	122-03-2
	NPASS ID	NPC252067
	CHEMBL ID	CHEMBL161577
NP Activity Charts	Click to show/hide
Activity Info

The Content Variation of Natural Product Induced by Different Factor(s)
Species Name: Artemisia annua
	Factor Name: Cultivar Comparison				[1]
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: 0.1 %
Artemisia annua cv. Jeevanraksha			Aerial parts	India		NP Content: 0.1 %
Species Name: Artemisia ferganensis
	Factor Name: Developmental Stage Variation				[2]
Species Info Factor Info
Experiment Detail		The leaves of aerial parts were collected in Heshuo county of Xinjiang province in China in July 2003 (a vegetative stage), June 2003 (a budding stage); and August 2003 (a flowering stage), respectively. Click to Show/Hide
Factor Function		Only 23 constituents were present at the budding stage, while 24 and 26 at the flowering and vegetative stages, respectively. p-Cymene and gamma-terpinene were not detected at the vegetative stage of the plant. During the budding stage, butyric, beta-caryophyllene, geranyl acetate and cis-jasmone could not be detected. Benzaldehyde was observed only at the vegetative stage. Variations were also observed in quantity. In all cases the analyzed oils were characterized by the high concentration of alpha-thujone, ranging in amount from 37.0% at the vegetative stage to 54.8% at the budding stage. The concentration of alpha-thujone at the flowering stage (49.0%) was lower than the budding stage, but higher than the vegetative stage. The concentration of cis-chrysanthenyl acetate varied between 23.5% and 7.2%, respectively, at the vegetative and budding stages. At the vegetative stage the concentration of 1,8-cineole was observed to be the lowest. It was highest at the budding stage, representing 10.4%, then decreased gradually to 8.8% at the flowering stage. The concentration of beta-thujone was relatively low at the vegetative stage, representing 8.6%, and then increased to 10.5% at the budding stage. When flowers appeared it was found to vary a little. Finally, the concentration of sabinyl acetate ranged from 10.2% (vegetative stage) to 6.5% (flowering stage). Click to Show/Hide
Factor			Part	Location		NP Content
Vegetative stage			Leaves	Heshuo, Xinjiang, China		NP Content: 0.4 %
Budding stage			Leaves	Heshuo, Xinjiang, China		NP Content: 0.3 %
Aerial part: Flowering stage			Leaves	Heshuo, Xinjiang, China		NP Content: 0.3 %
Species Name: Artemisia verlotiorum
	Factor Name: Developmental Stage Variation				[3]
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: full flowering stage			Aerial parts	Marseille, France		NP Content: 0.1 %
Species Name: Baccharis spartioides
	Factor Name: Altitude Variation				[4]
Species Info Factor Info
Experiment Detail		Aerial parts of endemic pichana were harvested in December 1996 at different localities of northern Patagonia. Origin: Planicie Banderita, Dept. Confluencia, Province of NeuquCn. Habitat: altitude, 327 m; average temperature in the station, 21.8 ℃; annual precipitation, 125 mm; sandy soils. Aerial parts (5 kg, 2 kg of dried material;humidity, 11%) from four well developed plants at the fullflowering stage (December, 1996). Sample 2 : Origin: RincBn de 10s; Sauces, Dept. of Pehuenclies, Province of Neuqukn. Habitat: altitude, 750 m; average temperature in the station, 20.9 ℃; annual precipitation, 147 mm; sandy and gritty salty soils. Aerial parts (5 kg, 1.85 kg of dried material, humidity, 10%), from two well developed plants at the full flowering stage, and after several days copious rains (December, 1996). Sample 3: Origin: Coronel GBmez, Dept. General Roca, Province of Rio Negro. Habitat: altitude, 242 m; average temperature in the station, 22.5 ℃; annual precipitation, 179 mm; sandy and stony soils. Aerial parts (4.5 kg, 1.3 kg of dried material, humidity, 9%), from 12 young plants at the beginning flowering stage (December, 1996). Click to Show/Hide
Factor Function		Fifty-four components, representing approximately 84.6-97.4% of the oil samples, were identified. The samples consisted mainly of hydrocarbons and oxygenated monoterpenes. The major constituents were limonene (28.7-56.7%), 6R-7R-bisabolone (3.2-9.1%), sabinene (0.1-11.0%) and citronellal (2.4-5.2%). Significant differences among the content of the three samples could be the result of changes in the climatic conditions (sample 2: Rincon de los Sauces, Province of Neuquen, after strong rains) or by translocations in different parts of the plant (sample 3: Coronel Gomez, Province of Rio Negro, more leaves and less stems). Click to Show/Hide
Factor			Part	Location		NP Content
Locality: Planicie Banderita, Province of Neuquen; Altitude 327 m			Aerial parts	Patagonia, Argentina		NP Content: 0.9 %
Locality: Rincon de los Sauces, Province of Neuquen; Altitude 750 m			Aerial parts	Patagonia, Argentina		NP Content: 0.2 %
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m			Aerial parts	Patagonia, Argentina		NP Content: 1.8 %
*Species Name: Citrus sinensis* (Hongjiang)**
	Factor Name: Variety Comparison				[5]
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. Click to Show/Hide
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. Click to Show/Hide
Factor			Part	Location		NP Content
Citrus sinensis var. Hongjiang			Fruits	China		NP Content: < 0.005 %
Citrus sinensis var. Sihui			Fruits	China		NP Content: < 0.005 %
Species Name: Ichthyothere terminalis
	Factor Name: Locality Variation				[6]
Species Info Factor Info
Experiment Detail		The leaves and stems of Ichthyothere terminalis were collected at Marapanim, PA (sample A) and Manaus, AM (sample B). Click to Show/Hide
Factor Function		The chief constituent found in the leaf oil of sample of, I. terminalis collected at Marapanim (PA) was sabinene (18.0%). The leaf oil of I. terminalis collected at Manaus (AM) was dominated by alpha-pinene (19-8%), sabinene (14.8%) and limonene (35.8%), while the main components identified in the stem oil were alpha-pinene (13.9%) and limonene (20.0%). Click to Show/Hide
Factor			Part	Location		NP Content
Leaves: Manaus, Brazil			Leaves	Brazil		NP Content: 0.4 %
Leaves: Marapanim, Brazil			Leaves	Brazil		NP Content: 0.4 %
Species Name: Porophyllum ruderale
	Factor Name: Harvest Time Variation				[7]
Species Info Factor Info
Experiment Detail		Seeds of P. ruderale were collected from wild plants found on the campus of the Federal University of Vicosa, Minas Gerais state (Brazil), in September 2000. The seeds were cultivated in a greenhouse during the period of February to May 2001; 60 days after sowing, the leaves and flowers were collected at regular intervals of 15 days for the oil isolation. Click to Show/Hide
Factor Function		The oil content found for the leaves of P. ruderale varied during the period of 60 to 120 days, as follows: 13.8 mg/100 g of fresh material after 60 days; 7.5 mg/100 g (75 days); 23.1 mg/100 g (90 days); 10.6 mg/100 g (105 days); 12.5 mg/100 g (120 days). The first floral buds were collected after 105 days of sowing, and its oil content was 45.1 mg/100 g of fresh material. A significant decrease in the production of oil from the buds was observed after 120 days of sowing, when only 23.0 mg oil/100 g of fresh material was obtained. During the period of 90 days to 105 days, a significant decrease in leaf oil content was observed, at the same time the plants were flowering. This data suggests the plants were relocating their resources to produce more oil in the floral buds. Click to Show/Hide
Factor			Part	Location		NP Content
Flower: (Harvesting time: after 120 days of sowing)			Flowers	Minas Gerais state, Brazil		NP Content: 0.1 %
Leaf: (Harvesting time: after 90 days of sowing)			Leaves	Minas Gerais state, Brazil		NP Content: 0.3 %
Species Name: Salvia euphratica
	Factor Name: Variety Comparison				[8]
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. Click to Show/Hide
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. Click to Show/Hide
Factor			Part	Location		NP Content
Salvia euphratica var. euphratica			Flowering aerial parts	Turkey		NP Content: 0.8 %
Salvia euphratica var. euphratica			Flowering aerial parts	Turkey		NP Content: 0.1 %
Salvia euphratica var. leiocalycina			Flowering aerial parts	Turkey		NP Content: 1.5 %
Species Name: Satureja cuneifolia
	Factor Name: Developmental Stage Variation				[9]
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: Full Blooming stage			Aerial parts	Middle Anatolia, Turkey		NP Content: 0.2 %
Aerial part: Flowering stage			Aerial parts	Middle Anatolia, Turkey		NP Content: <0.1 %
Species Name: Tanacetum larvatum
	Factor Name: Locality Variation				[10]
Species Info Factor Info
Experiment Detail		Aerial parts of T. larvatum were collected in July and August during a five-year period, starting in 2001, in Montenegro on several locations: Planinica (Sample a), Visitor (Sample b) and Sinjajevina (Sample c). Click to Show/Hide
Factor Function		Sixty-four components were identified, representing 83.1%, 96.6% and 89.4% of the total oils content in the Planinica [Sample a], Visitor [Sample b] and Sinjajevina [Sample c], respectively. The major constituent in Samples a and b , was oxygenated monoterpene, trans-sabinyl acetate (38.1% and 55.8% respectively). Monoterpene hydrocarbons, beta-pinene (13.5%) and santolinatriene (30.6%), were found to be the dominant components in Sample c. The toxic trans-sabinyl acetate was present only in traces in this sample. trans-Chrysanthenyl acetate, as one of major components in feverfew essential oil, has not been previously identified in the investigated essential oils. Click to Show/Hide
Factor			Part	Location		NP Content
Locality: Visitor, Montenegro			Aerial parts	Montenegro		NP Content: 0.3 %
Species Name: Thymus striatus
	Factor Name: Locality Variation				[11]
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	Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
2	Seasonal Analyses of the Essential Oil of Artemisia ferganensis
3	Chemical Variation in the Oil of Artemisia verlotiorum Lamotte of French Origin Harvested at a Vegetative Stage and During Flowering
4	Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
5	Volatile Constituents of the Peel Oils of Several Sweet Oranges in China
6	Volatile Constituents of Ichthyothere terminalis and I. cunabi
7	Essential Oil from Leaves and Flowers of Porophyllum ruderale (Jacq.) Cassini (Asteraceae)
8	The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
9	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.
10	Intraspecific Variation of Tanacetum larvatum Essential Oil
11	Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey

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