2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00025 |
| Mol. Weight | 136.238 g/mol |
| LogP | 3.22 |
| Water solubility | In water, 13.8 mg/L at 25 °C |
| Hydrogen Bond Donor | 0 |
| Hydrogen Bond Acceptor | 0 |
| Rotatable Bonds | 1 |
| XLogP3-AA | 3.4 |
| Identifiers | |
|---|---|
| Formula | C10H16 |
| PubChem CID | 440917 |
| FEMA | 2633 |
| Flavor Profile | Citrus Odor, Fresh, Citrus Taste, Fruity, Lemon |
| Smiles | C=C(C)[C@H]1CC=C(C)CC1 |
| InChl Key | XMGQYMWWDOXHJM-JTQLQIEISA-N |
| InChl | InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1 |
| CAS Registry Number | 5989-27-5, 65996-98-7, 5989-27-5, 68606-81-5 |
| IUPAC Systematic Name | (4R)-1-methyl-4-prop-1-en-2-ylcyclohexene |
Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets
Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)
| English Name | Pinyin Name (Chinese Name) | Latin Name | Properties in TCM | merdians | View Graph |
|---|---|---|---|---|---|
| Chinese Star Anise | Ba Jiao Hui Xiang (八角茴香) | Anisi Stellati Fructus | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Common Ginger Dried Rhizome | Gan Jiang (干姜) | Zingiberis Rhizoma | Hot, Pungent | Lung, Spleen, Stomach, Heart, Kidney | View Graph |
| Cassiabarktree Twig | Gui Zhi (桂枝) | Cinnamomi Ramulus | Warm, Pungent, Sweet | Lung, Bladder, Heart | View Graph |
| Siebold Wildginger Equivalent plant: Asarum hetero | Xi Xin (细辛) | Asari Radix Et Rhizoma | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Lily Magnolia Buds Equivalent plant: Magnolia lili | Xin Yi (辛夷) | Magnoliae Flos | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Wild Mint | Bo He (薄荷) | Menthae Haplocalycis Herba | Cool, Pungent | Liver, Lung | View Graph |
| Doubleteeth Pubescent Angelica Equivalent plant: H | Du Huo (独活) | Angelicae Pubescentis Radix | Warm, Pungent, Bitter | Spleen, Liver | View Graph |
| Divaricate Saposhnikovia | Fang Feng (防风) | Saposhnikoviae Radix | Warm, Pungent, Sweet | Lung, Bladder, Heart | View Graph |
| Chinese Ligusticum Equivalent plant: Ligusticum je | Gao Ben (藁本) | Ligustici Rhizoma Et Radix | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Myrrh | Mo Yao (没药) | Myrrha | Neutral, Pungent, Bitter | Spleen, Liver, Heart, Kidney | View Graph |
| Incised Notopterygium Equivalent plant: Notoptery | Qiang Huo(羌活) | Notopterygii Rhizoma Et Radix | Warm, Bitter, Pungent | Spleen, Large Intestine, Stomach, Gallbladder, Three End | View Graph |
| Frankincense, Olibanum | Ru Xiang (乳香) | Olibanum | Warm,Bitter, Pungent | Spleen, Lung | View Graph |
| Fresh Common Ginger | Sheng Jiang(生姜 ) | Zingiber Rhizoma Recens | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Haichow Elsholtzia | Xiang Ru (香薷) | Moslae Herba | Minor Warm,Pungent | Lung, Spleen, Stomach | View Graph |
| Dahurian Rhododendron | Man Shan Hong (满山红) | Rhododendri Daurici Folium | Cold, Pungent, Bitter | Liver, Heart, Lung | View Graph |
| Medicinal Indianmulberry | Ba Ji Tian(巴戟天) | Morindae Officinalis Radix | Warm, Pungent, Sweet | Lung, Bladder, Heart | View Graph |
| Dahurian Angelica | Bai Zhi(白芷) | Angelicae Dahuricae Radix | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Chinese Thorowax Equivalent plant: Bupleurum scorz | Chai Hu(柴胡) | Bupleuri Radix | Minor cold, Pungent, Bitter | Liver, Gallbladder, Lung | View Graph |
| Chinese Angelica Equivalent plant: Phlojodicarpus | Dang Gui (当归) | Angelicae Sinensis Radix | Warm,Pungent,Sweet | Spleen,Liver,Heart | View Graph |
| Fleshfingered Citron | Fo Shou (佛手) | Citri Sarcodactylis Fructus | Warm, Pungent, Sour, Bitter | Lung, Spleen, Stomach, Liver, Kidney | View Graph |
| bark of Officinal magnolia | Hou Pu(厚朴) | Magnoliae Officinalis Cortex | Warm, Pungent, Bitter | Spleen, Liver | View Graph |
| Common Turmeric Equivalent plant: Curcuma aromati | Jiang Huang (姜黄) | Curcumae Longae Rhizoma | Warm, Pungent, Bitter | Spleen, Liver | View Graph |
| Fineleaf Schizonepeta | Jing Jie (荆芥) | Schizonepetae Herba | Minor Warm, Pungent | Lung, Liver | View Graph |
| Bush Redpepper | La Jiao (辣椒) | Capsici Fructus | Hot, Pungent | Lung, Spleen, Stomach, Heart, Kidney | View Graph |
| Fortune Eupatorium Equivalent plant: Eupatorium f | Pei Lan(佩兰) | Eupatorii Herba | Neural, Pungent | Lung,Spleen,Stomach | View Graph |
| rhizome of Obscured Homalomena | Qian Nian Jian(千年健) | Homalomenae Rhizoma | Warm, Bitter, Pungent | Spleen, Large Intestine, Stomach, Gallbladder, Three End | View Graph |
| Sandalwood | Tan Xiang(檀香) | Santali Albi Lignum | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Apple Mint | Yu Xian Cao(鱼腥草) | Houttuyniae Herba | Cold, Pungent | Lung | View Graph |
| Perilia Fruit | Zi Su Zi (紫苏子) | Perillae Fructus | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Zedoray Rhizome | E Zhu (莪术) | Curcumae Rhizoma | Warm, Pungent, Bitter | Spleen, Liver | View Graph |
| Herba Schizonepetae | Jing Jie Sui (荆芥穗) | Schizonepetae Spica | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Tokyo Violet | Zi Hua Di Ding (紫花地丁) | Peucedani Decursivi Radix | Cold, Pungent, Bitter | Liver, Heart, Lung | View Graph |
| Villous Amomum Equivalent plant: Amomum xanthioide | Sha Ren (砂仁) | Amomi Fructus | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Dryobalanops aromatica | Bing Pian(冰片) | Borneol | Minor cold,Pungent,Bitter | Lung,Spleen,Heart | View Graph |
| Fructus Xanthii sibirici | Cang Er Zi(苍耳子) | fruit of Siberian Cockleblur | Warm,Pungent,Bitter | Lung,Spleen,Liver | View Graph |
| Cnidium monnieri | She Chuang Zi(蛇床子) | Common Cnidium | Warm,Pungent,Bitter | Lung,Spleen,Liver | View Graph |
| Evodia rutaecarpa | Wu Zhu Yu(吴茱萸) | Medicinal Evodia Equivalent plant: Evodia rutaecar | Pungent, bitter, hot | Liver, spleen,stomach | View Graph |
D-limonene (4-isopropenyl-1-methylcyclohexene), is a major constituent in several citrus-derived essential oils (e.g. orange, peel, lemon, mandarin, lime,
grapefruit,etc.) and has been considered as generally regarded as safe (GRAS) for use as a flavouring agent and food preservative. D-Limonene has been
considered to be a safer alternative compared to synthetic antimicrobial food additives. D-limonene is a commonly used flavor additive in food, beverages
and fragrances for its pleasant lemon-like odor. D-limonene have become a priority in the food industry in terms of improving the safety of food products
by acting against foodborne pathogens. D-Limonene is the main compound contained in all citrusderived essential oils (EOs). It is widely used as a
flavouring agent in commercial applications such as the food and beverage industry due to its transparency and its pleasant citrus fragrance. D-limonene
is one of the most common terpenes in nature. D-limonene is considered to have fairly low toxicity.
Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.
1 Bacanlı M, Anlar H G, Aydın S, et al. d-Limonene ameliorates diabetes and its complications in streptozotocin-induced diabetic rats[J]. Food and Chemical Toxicology, 2017, 110: 434-442.
2 Murthy K N C, Jayaprakasha G K, Patil B S. D-limonene rich volatile oil from blood oranges inhibits angiogenesis, metastasis and cell death in human colon cancer cells[J]. Life sciences, 2012, 91(11-12): 429-439.
3 Lu X, Zhan L, Feng B, Qu M, Yu L, Xie J. Inhibition of growth and metastasis of human gastric cancer implanted in nude mice by D-limonene. World J Gastroenterol 2004;10:2140–4.
4 Lu X G, Zhan L B, Feng B A, et al. Inhibition of growth and metastasis of human gastric cancer implanted in nude mice by d-limonene[J]. World Journal of Gastroenterology: WJG, 2004, 10(14): 2140.
5 1 Uedo N, Tatsuta M, Iishi H, Baba M, Sakai N, Yano H, Otani T. Inhibition by D-limonene of gastric carcinogenesis induced by N-methyl-N’-nitro-N-nitrosoguanidine in Wistar rats. Cancer Lett 1999; 137: 131-136
6 2 Broitman SA, Wilkinson J 4th, Cerda S, Branch SK. Effects of monoterpenes and mevinolin on murine colon tumor CT-26 in vitro and its hepatic “metastases” in vivo. Adv Exp Med Biol 1996; 401: 111-130
7 3 Kaji I, Tatsuta M, Iishi H, Baba M, Inoue A, Kasugai H. Inhibition by d-limonene of experimental hepatocarcinogenesis in Sprague-Dawley rats does not involve p21(ras) plasma membrane association. Int J Cancer 2001; 93: 441-444
8 4 Witschi H, Uyeminami D, Moran D, Espiritu I. Chemoprevention of tobacco-smoke lung carcinogenesis in mice after cessation of smoke exposure. Carcinogenesis 2000; 21: 977-982
9 5 Stratton SP, Dorr RT, Alberts DS. The state-of-the-art in chemoprevention of skin cancer. Eur J Cancer 2000; 36: 1292-1297
10 6 Guyton KZ, Kensler TW. Prevention of liver cancer. Curr Oncol Rep 2002; 4: 464-470
11 7 Nakaizumi A, Baba M, Uehara H, Iishi H, Tatsuta M. d-limonene inhibits N-nitrosobis (2-oxopropyl) amine induced hamster pancreatic carcinogenesis. Cancer Lett 1997; 117: 99-103
12 Zhang Z, Vriesekoop F, Yuan Q, et al. Effects of nisin on the antimicrobial activity of D-limonene and its nanoemulsion[J]. Food chemistry, 2014, 150: 307-312.
13 Murali R, Karthikeyan A, Saravanan R. Protective effects of D‐limonene on lipid peroxidation and antioxidant enzymes in streptozotocin‐induced diabetic rats[J]. Basic & clinical pharmacology & toxicology, 2013, 112(3): 175-181.
14 Ahmad M, Khan T H, Ansari M N, et al. Enhanced wound healing by topical administration of d-limonene in alloxan induced diabetic mice through reduction of pro-inflammatory markers and chemokine expression[J]. BMC genomics, 2014, 15(2): P29.
15 Najjar M B, Kashtanov D, Chikindas M L. ε‐Poly‐l‐lysine and nisin A act synergistically against Gram‐positive food‐borne pathogens Bacillus cereus and Listeria monocytogenes[J]. Letters in applied microbiology, 2007, 45(1): 13-18.
16 Zahi M R, El Hattab M, Liang H, et al. Enhancing the antimicrobial activity of d-limonene nanoemulsion with the inclusion of ε-polylysine[J]. Food chemistry, 2017, 221: 18-23.
17 Chikhoune A, Hazzit M, Kerbouche L, et al. Tetraclinis articulata (Vahl) Masters essential oils: chemical composition and biological activities[J]. Journal of essential oil research, 2013, 25(4): 300-307.
18 Vuuren S F, Viljoen A M. Antimicrobial activity of limonene enantiomers and 1, 8‐cineole alone and in combination[J]. Flavour and Fragrance Journal, 2007, 22(6): 540-544.
19 Sun J. D-Limonene: safety and clinical applications[J]. Alternative Medicine Review, 2007, 12(3): 259.
20 Sonu K S, Mann B, Sharma R, et al. Physico-chemical and antimicrobial properties of d-limonene oil nanoemulsion stabilized by whey protein–maltodextrin conjugates[J]. Journal of food science and technology, 2018, 55(7): 2749-2757.
21 Zahi M R, Liang H, Yuan Q. Improving the antimicrobial activity of D-limonene using a novel organogel-based nanoemulsion[J]. Food Control, 2015, 50: 554-559.
22 Ravichandran C, Badgujar P C, Gundev P, et al. Review of toxicological assessment of d-limonene, a food and cosmetics additive[J]. Food and Chemical Toxicology, 2018.
23 Todaka M, Kowhakul W. The flash points and thermal behaviors of diesel blends with biodiesels, α-pinene, d-limonene and caffeic acid as antioxidants[J]. Journal of Thermal Analysis and Calorimetry, 1-11.
24 Lopresto C G, Petrillo F, Casazza A A, et al. A non-conventional method to extract D-limonene from waste lemon peels and comparison with traditional Soxhlet extraction[J]. Separation and Purification Technology, 2014, 137: 13-20.
25 Ruiz-Pérez N J, González-Ávila M, Sánchez-Navarrete J, et al. Antimycotic activity and genotoxic evaluation of citrus sinensis and citrus latifolia essential oils[J]. Scientific reports, 2016, 6: 25371.
26 Noguerol-Pato R, González-Álvarez M, González-Barreiro C, et al. Aroma profile of Garnacha Tintorera-based sweet wines by chromatographic and sensorial analyses[J]. Food chemistry, 2012, 134(4): 2313-2325.
27 Mozell M M. Evidence for sorption as a mechanism of the olfactory analysis of vapours[J]. Nature, 1964, 203(4950): 1181.
28 Crowell P L, Elson C E, Bailey H H, et al. Human metabolism of the experimental cancer therapeutic agentd-limonene[J]. Cancer chemotherapy and pharmacology, 1994, 35(1): 31-37.
29 Igimi H, Hisatsugu T, Nishimura M. The use ofd-limonene preparation as a dissolving agent of gallstones[J]. The American journal of digestive diseases, 1976, 21(11): 926-939.
30 Elegbede J A, Elson C E, Qureshi A, et al. Inhibition of DMBA-induced mammary cancer by the monoterpene d-limonene[J]. Carcinogenesis, 1984, 5(5): 661-664.
31 Flavor and Extract Manufacturers’ Association (FEMA), 1991. D-limonene Monograph. Washington, DC. pp. 1–4.
32 International Agency for Research on Cancer. Some chemicals that cause tumours of the kidney or urinary bladder in rodents and some other substances[J]. IARC monographs on the evaluation of carcinogenic risks to humans, 1999, 73: 131-182.
33 Karlberg A T, Magnusson K, Nilsson U. Influence of an anti-oxidant on the formation of allergenic compounds during auto-oxidation of d-limonene[J]. The Annals of occupational hygiene, 1994, 38(2): 199-207.
34 Kim Y W, Kim M J, Chung B Y, et al. Safety evaluation and risk assessment of d-limonene[J]. Journal of Toxicology and Environmental Health, Part B, 2013, 16(1): 17-38.
35 Murali R, Saravanan R. Antidiabetic effect of d-limonene, a monoterpene in streptozotocin-induced diabetic rats[J]. Biomedicine & Preventive Nutrition, 2012, 2(4): 269-275.
36 Wolkoff P, Clausen P A, Larsen K, et al. Acute airway effects of ozone-initiated d-limonene chemistry: importance of gaseous products[J]. Toxicology letters, 2008, 181(3): 171-176.
37 Zhu Y, Chen Z, Yang Y, et al. Using d-limonene as the non-aromatic and non-chlorinated solvent for the fabrications of high performance polymer light-emitting diodes and field-effect transistors[J]. Organic Electronics, 2015, 23: 193-198.
38 Chappell S A, Walsh T, Walker R A, et al. Loss of heterozygosity at the mannose 6-phosphate insulin-like growth factor 2 receptor gene correlates with poor differentiation in early breast carcinomas[J]. British journal of cancer, 1997, 76(12): 1558.
39 Vigushin D M, Poon G K, Boddy A, et al. Phase I and pharmacokinetic study of D-limonene in patients with advanced cancer[J]. Cancer chemotherapy and pharmacology, 1998, 42(2): 111-117.
40 https://en.wikipedia.org/wiki/Limonene