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รองศาสตราจารย์ ดร อรพิน เกิดชูชื่น รองศาสตราจารย์ ดร ณัฎฐา เลาหกุลจิตต์

รองศาสตราจารย์ ดร อรพิน เกิดชูชื่น รองศาสตราจารย์ ดร ณัฎฐา เลาหกุลจิตต์ School of Bioresources and Technology King Mongkut’s University of Technology Thonburi , Bangkok. Introduction.

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รองศาสตราจารย์ ดร อรพิน เกิดชูชื่น รองศาสตราจารย์ ดร ณัฎฐา เลาหกุลจิตต์

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  1. รองศาสตราจารย์ดร อรพิน เกิดชูชื่น รองศาสตราจารย์ดรณัฎฐา เลาหกุลจิตต์ School of Bioresources and Technology King Mongkut’s University of Technology Thonburi , Bangkok

  2. Introduction Aromatic and medicinal plants are important for pharmaceutical, food and fragrance industries although they contain a small fractionof volatile oil. Essential oils are interested in aromatherapy for healing, cleansing, preservative, and mood-elevating attributes.

  3. Essential oils refer to the subtle, aromatic and volatile liquids extracted from the flowers, seeds, leaves, stems, bark and roots of herbs, bushes, shrubs and trees . Chemically, in the essential oils that can derived to primarily composed of mono- and sesquiterpenes and aromatic etc.

  4. Essential oils found in 108 families and > 2000 species. http://www.nazflora.org/Dicots.htm

  5. Umbelliferae http://en.wikipedia.org/wiki/Umbelliferae

  6. Coriander Kingdom: Plantae Family: Umbelliferae Genus: Coriandrum Species: C. sativum Binomial name: Coriandrumsativum • All parts of the plant are edibleused in cooking. • seeds are used a carminative and a digestive aidthe relief of • anxiety and insomnia in Iran • It helps to detoxify the body and to stimulatethe spleen.

  7. Coriander oil has a sweet, spicy, warm smell, is nearly colorless to pale yellow and has a watery viscosity. The therapeutic properties of coriander oil are analgesic, aphrodisiac, antispasmodic, carminative, depurative, deodorant, digestive, carminative, fungicidal, lipolytic, stimulant and stomachic.

  8. Commercial Used Herrero et al., 2010

  9. Chemical composition of essential oil from Coriander . 53 compounds are detected γ-Terpinene (14.42%) Geranyl acetate (17.57%) Linalool (37.65%) α-Cedrene (3.87%) Bhuiyan, et.al., 2009

  10. Chemistry of essential oils The complicated volatile compounds in essential oil could be divided into 4 groups: Aliphatic compound Benzene derivatives Terpene derivatives Others compound http://www.wikipedia.org/

  11. Aliphatic compound In aliphatic compounds, carbon atoms can be joined together in straight chains, branched chains, or non-aromatic rings • Aliphatic Alcohol • cis-3-hexen-1-ol cis-2-hexen-1-ol 1-octen-3-ol • Aliphatic aldehydes • n-octanaltrans-2-hexanal http://isostar.ccdc.cam.ac.uk/html/classes/Ligand_Acyclic_links_O_C_H_only.html

  12. Aliphatic ketones • 3-hydroxy-2-butanone (acetoin) • diacetyl (2,3-butanedione) • Aliphatic esters • C6 alcohol-acetate : fruity notes • C8-12 acetate : blossom fragrance • C12 : conifer notes • acetate-ester: fatty-soapy odour • Ethyl acetate Benzyl acetate Linalyl acetate http://isostar.ccdc.cam.ac.uk/html/classes/Ligand_Acyclic_links_O_C_H_only.html

  13. Benzene derivatives Benzene is an organicchemical compound with the molecular formula (C6H6 ) n Benzene is an aromatic hydrocarbon, a cyclic hydrocarbon with a continuous pi bond • Hydrocarbon • Benzenoid alcohol • Cinnamic-alcohol Cinnamaldehyde Phenylacetaldehyde http://en.wikipedia.org/wiki/Benzene

  14. 3. Benzenoid ketone 4. Ester of aromatic alcohols andaliphatic acids Benzylacetate Benzyl benzoate Phenylethyl acetate http://en.wikipedia.org/wiki/Benzene

  15. Terpene derivatives Terpenes are derived biosynthetically from units of isoprene, which has the molecular formula (C5H8 ) n. That may be classified by the number of terpene units in the molecule. http://en.wikipedia.org/wiki/Terpene

  16. Monoterpene the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings. http://en.wikipedia.org/wiki/Terpene

  17. Sesquiterpenes The molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. http://en.wikipedia.org/wiki/Terpene

  18. Diterpenes Diterpenes are composed for four isoprene units and have the molecular formula C20H32 Retinol : Triterpenes Triterpenes consist of six isoprene units and have the molecular formula C30H48 Lanosterol : http://en.wikipedia.org/wiki/Terpene

  19. Other compounds http://www.wikipedia.org/

  20. The volatile oil composition may change from the natural odor depending on the extraction method (Anitescu et al, 1997).

  21. The volatile oil composition may change from the natural odor depending on the extraction method Anitescu et al, 1997

  22. Plant extracts Production

  23. Extraction Flavor + fragrance ที่สกัดจากพืชเรียก “pomades, concretes, absolutes, resinoids or tincture 1.  Pomades ประกอบด้วยไขมันที่มีสารให้กลิ่นหอมอยู่เตรียมโดยวิธี hot or cold enfleurage จากดอกไม้ -   Hot enfleurage วิธีเก่าแก่ในการเก็บรักษากลิ่นหอมโดยนำดอกไม้หรือส่วนต่างๆของพืชจุ่มใน wax เหลว + ร้อน -   Cold enfleurage ใช้ไขมันเป็นตัว adsorp volatile component ที่ปล่อยจากดอกไม้โดยเอาดอกไม้สดใส่ไว้ในชั้นไขมันซึ่งไขมันประกอบด้วย lard + beef tallow ซึ่ง spread บนกระจกแก้วในภาชนะปิดเป็นวิธีใช้แทนการสกัดด้วย solvent

  24. 2. Concretes สกัดส่วนต่างๆของพืชด้วย solvent ชนิด non polar solvent (toluene, hexane, petroleum ether) เมื่อระเหยส่วนที่เหลือจะมี volatile fragrance + non volatile รวมทั้ง wax cpds. Concrete มีลักษณะเหมือน pomades ไม่ละลายใน alc ... มีข้อจำกัดในการนำมาใช้ perfume แต่ใช้ให้กลิ่นสบู่ Concrete สกัดมาจากดอกไม้ (กุหลาบมะลิเป็นต้น) ส่วนตางๆของพืช (lavender, violet leaf เป็นต้น) 3. Absolutes เตรียมจาก concrete ละลายใน ethanol ตกตะกอนที่ temp ต่ำกรองระเหย EtOH ออก wax – free เรียก absolute ... ละลายได้ใน EtOH ใช้ perfume ingredients 4. Resinoids เตรียมจากยางไม้ (plant exudates) สกัดด้วย solvent เช่น methanol, EtOH, Toluene  yield 50 – 95% product เหนียวทำเจือจางเติม phthalates หรือ benzyl benzoate เพื่อปรับปรุงคุณสมบัติการไหลและการนำไปใช้ resinoid ประกอบด้วย nonvolatile + resinoid cpds. ต่างจาก oleoresin ซึ่งได้จาก pepper, ginger, vanilla oleoresins ใช้ solvent สกัดจาก spices solvent ที่ใช้ขึ้นกับชนิด spices หรือ supercritical CO2เป็นตัวสกัด pepper + ginger oleoresins มี volatile aroma + pungency 5. Tinctures เป็นสารที่ละลายใน alc. เตรียมโดย Treat natural raw material ด้วย ethanol ผสมกับน้ำซึ่ง solvent เหล่านี้สามารถละลายสารที่สกัดได้จากพืชชนิดต่างๆ Tinctures บางครั้งเรียกว่า Infusion

  25. Extraction methods • Expression • Distillation • -Hydrodistillation • -Steam distillation • - Simultaneous distillation extraction • - Vacuum distillation • Solvent extraction • - Enflurage • - Liquid-liquid extraction • - Soild-liquid extraction • - Supercritical fluid extraction http://en.wikipedia.org/wiki/Essential_oil#Production

  26. 1. Expression • Advantage • Low cost • simple • Disadvantage • - High energy • - Long time http://www.weloveshopping.com/template/e1/showproduct.php?shopid=221389&productid=CHH8

  27. 2. Distillation Distillation is a method of separating mixtures based on differences in their volatilities in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction. http://en.wikipedia.org/wiki/Distillation

  28. Hydrodistillation • Traditional method of extraction • Advantage • -Easy separation • Disadvantage • - Combustion of the • sample • - Degradation of • volatile compound http://en.wikipedia.org/wiki/Distillation#Hydrodistillation

  29. Steam distillation • distilling compounds • which are heat-sensitive http://en.wikipedia.org/wiki/Distillation#Steam_distillation

  30. Simultaneous distillation extraction (SDE) • Advantage • - Semi-volatile and heat- • stable component • High recovery • - rapid • Disadvantage • - concrete • Degradation of volatile • compound • - Thermal degradation http://en.wikipedia.org/wiki/Distillation

  31. Vacuum distillation • low temperature distillation • Principle: pressure above • mixture is reduced to less • than its vapor pressure http://en.wikipedia.org/wiki/Vacuum_distillation

  32. 3. Solvent extraction • Enfleurage • Enfleurage uses odorless • fats that are solid at room • temperature http://en.wikipedia.org/wiki/Enfleurage

  33. Liquid-liquid extraction (LLE) • Partition • Extraction of a substance with • different densities http://en.wikipedia.org/wiki/Liquid-liquid_extraction

  34. Soild-liquid extraction • Base on like dissolve like • Use solvent to separate desired • compound from solid sample • Advantage • Analyze in one extraction step • Disadvantage • - Loss of certain compounds • - The time for an average • Soxhlet extraction ranges • from 1 to 72 h. Soxhlet extractor http://en.wikipedia.org/wiki/Liquid

  35. Supercritical fluid extraction (SFE) Supercritical fluids provide a higher solubility of the components of the volatile oil, as well as improved mass-transfer rates. Moreover, the manipulation of parameters as temperature and pressure leads to the extraction of different components. Reverchon and De Marco, 2006

  36. Supercritical fluid extraction (SFE)

  37. Supercritical fluid extraction (SFE) - Dense gases - Critical temperature & pressure - Resemble both liquids & gases

  38. Criticalpropertiesofvarioussolvents Reid et al., 1987

  39. Super Critical CO2 Extraction DISADVANTAGE Boilingpoint, Artifactformationpartiallossofextractedvolatiles ADVANTAGES Easytoremove,Notharmful, odorless, tasteless, nonflammable,Inexpensiveinhighpurity,moderatecondition = 310C 74 bar, no degradation ---->labile flavorcompoundsselectivity, aroma & flavor-->resemblance tooriginalmaterial

  40. SOLUBILITY UNDER LIQUID CO2 • 1.MW< 500 daltons • Low- mediumMWof halocarbon, aldehyde, keton, • ester, alcohol, ether • LowMW, nonpolar, aliphatichydrocarbons -- 20 carbons • 4.Polarorganic -- lowsolubility • 5. Polargroups -- OH, COOH, N decreasesolubility • Chorophyll, carotenoids, aminoacid, fruitacid • --->insoluble • Alkaloids, phenols, anilinecompounds • ----> poorsolubility

  41. The application of liquid CO2 HOP, OLEORESIN, Basils, VANILLA, ONIONOIL, CITRUSOIL, APPLEJUICE, PEAR, COFFEE, ORANGE, Coliander FLAVOR, FRAGRANCE, AND COLORANTS CONCERN HEALTH AND ENVIRONMENT Consumer demand, new, improved, natural, high quality

  42. SUPERCRITICAL REGION SUPERCRITICAL REGION TOTAL EXTRACTION SOLID Pressure (bar) FRACTIONATION LIQUID TRIPLE POINT CRITICAL POINT DEODERIZATION Pc = 73.8 bar Tc = 31.1 ˚c GAS Temperature (˚c) Laohakunjit .,2010

  43. Factor affecting on quality of extract by SFE • Temperature • Pressure • Particle size • Time Pourmortazavi et al., 2007 and Bensebia et al., 2009

  44. 2. Continuous Solvent Extraction Condenser Beverage sample Solvent (Ether) Holes at the bottom of the tube Water Bath

  45. Persicariaodorata • Common name : Vietnamese coriander • Thai name : Pak-Paeow • Family : Polygonaceae • Usually use for culinary herbs

  46. Suaedamaritima • Common name : Annual sea blite • Thai name : Cha-kram • Family : Amaranthaceae • Include in halophyte plant group • Salt content in the tissues is very high -> can act as antimicrobial agent

  47. Piper sarmentosum • Common name : Wild betel • Thai name : Cha-plu • Family : Piperaceae • Culinary and medicine herbs

  48. Application of essential oil in chicken meat Several type of plant has been use for preservatives in chicken meat No report about the application of essential oil or plant extract from Vietnamese coriander, annual sea blite and wild betel

  49. Extraction process Sample preparation Dry sample : 20 gr Composition : (1:2 w/v ratios) Hydrodistillation Solvent Extraction Dry sample : 500 gr Fresh sample : 1000 gr Time : 24 h. Ethanol Acetone Petroleum ether 24 hour extraction (1st extraction) 1st extracts Essential oil (dry and fresh sample) Residue 72 hour extraction (2nd extraction) 2nd extracts Residue Wax washing process Physical, chemical, and biological activity analysis absolutes

  50. Physical, chemical, and biological activity analysis The best plant extracts Application into the raw chicken meat

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