Grapefruit merkaptan

Grejpfrut merkaptan
Struktura	3D model
Nazivi
	IUPAC naziv 2-[(1R)-4-Metilcikloheks-3-en-1-il]propan-2-tiol
	Drugi nazivi 1-p-menten-8-tiol; α,α,4-trimetilcikloheks-3-en-1-metan tiol; tioterpineol
Identifikacija
CAS broj	71159-90-5 (racemat) ; 83150-78-1 (R enantiomer) ;
3D model (Jmol)	interaktivna slika;
ChemSpider	21163535 ;
ECHA InfoCard	100.072.886
EC broj	275-223-1
PubChem C ID	6427135;
UNII	7AT54D0N8R ;
	SMILES SC(C)(C)[C@@H]1CCC(C)=CC1; ; ; ; ; ;
Svojstva
Hemijska formula	C10H18S
Molarna masa	170,31 g/mol
Gustina	1,03 g/cm3
Tačka topljenja	25 (< 25 °C)
Tačka ključanja	58 (na 0,33 mmHg)
Opasnosti
GHS grafikoni
GHS signalna reč	Warning
GHS opis opasnosti	H302, H315, H319
GHS mere predostrožnosti	P264, P270, P280, P301+312, P302+352, P305+351+338, P321, P330, P332+313, P337+313, P362, P501
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	verifikuj (šta je ?)
	Reference infokutije

Grejpfrut merkaptan (grapefruit mercaptan) je prirodno organsko jedinjenje koje se nalazi u grejpfrutu. To je monoterpenoid koji sadrži tiolnu (poznatu i kao merkaptan) funkcionalnu grupu.

Strukturno, hidroksilna grupa terpineola je u ovom jedinjenju zamenjena tiolom, pa se ono naziva i tioterpineol. Isparljivi tioli obično imaju vrlo jake, često neprijatne mirise koji se mogu detektovati pri veoma niskim koncentracijama. Grejpfrut merkaptan ima veoma snažan, ali ne i neprijatan miris, i on je hemijski sastojak primarno odgovoran za aromu grejpfruta.^[3] Ova karakteristična aroma je svojstvo samo R enantiomera.^[4]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	1
Broj donora vodonika	1
Broj rotacionih veza	1
Particioni koeficijent^[5] (ALogP)	3,4
Rastvorljivost^[6] (logS, log(mol/L))	-2,2
Polarna površina^[7] (PSA, Å²)	38,8

Prag detekcije i upotreba

Čist grejpfrut merkaptan, ili ulja citrusa bogata ovim jedinjenjem, ponekad se koriste u industriji parfema i aroma kako bi se dobile citrusne note. Međutim, obe industrije aktivno traže zamene za grejpfrut merkaptane, jer su proizvodi njegovog razlaganja često veoma neprijatni za ljudsko čulo mirisa.

Prag detekcije za (+)-(R) enantiomer grejpfrut merkaptana je 3,4×10⁻⁵ ppb, ili ekvivalentno koncentraciji od 0,000034 nanograma po kubnom metru vazduha. Ovo je jedan od najnižih zabeleženih pragova detekcije mirisa.^[8]^[9]

Vidi još

Nootkaton, još jedno jedinjenje arome grejpfruta
Terpineol, analogno jedinjenje sa hidroksilnom grupom umesto tiola

Reference

^ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.
^ Buettner A.; Schieberle P. (1999). „Characterization of the Most Odor-Active Volatiles in Fresh, Hand-Squeezed Juice of Grapefruit (Citrus paradisi Macfayden)”. J. Agric. Food Chem. 47 (12): 5189—5193. PMID 10606593. doi:10.1021/jf990071l.
^ Lehmann D.; Dietrich A.; Hener U.; Mosandl A. (1994). „Stereoisomeric flavor compounds. LXX: 1-p-menthene-8-thiol: separation and sensory evaluation of the enantiomers by enantioselective gas chromatography-olfactometry”. Phytochemical Analysis. 6 (5): 255—257. doi:10.1002/pca.2800060506.
^ Ghose, A.K.; Viswanadhan V.N. & Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A. 102: 3762—3772. doi:10.1021/jp980230o.
^ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488—1493. PMID 11749573. doi:10.1021/ci000392t.
^ Ertl P.; Rohde B.; Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714—3717. PMID 11020286. doi:10.1021/jm000942e.
^ Schoenauer, Sebastian; Schieberle, Peter (2016). „Structure–Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1- p -Menthene-8-thiol”. Journal of Agricultural and Food Chemistry. 64 (19): 3849—3861. PMID 27121638. doi:10.1021/acs.jafc.6b01645.
^ Demole, E.; Enggist, P.; Ohloff, G. (1982). „1-p-Menthene-8-thiol: A powerful flavor impact constituent of grapefruit juice (Citrus parodisi MACFAYDEN)”. Helvetica Chimica Acta. 65 (6): 1785—1794. doi:10.1002/hlca.19820650614.

Literatura

Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (I изд.). Oxford University Press. ISBN 978-0-19-850346-0.
Smith, Michael B.; March, Jerry (2007). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th изд.). New York: Wiley-Interscience. ISBN 0-471-72091-7.
Katritzky A.R.; Pozharskii A.F. (2000). Handbook of Heterocyclic Chemistry (Second изд.). Academic Press. ISBN 0080429882.

Spoljašnje veze

Grapefruit mercaptan

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[2] Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.

[3] Buettner A.; Schieberle P. (1999). „Characterization of the Most Odor-Active Volatiles in Fresh, Hand-Squeezed Juice of Grapefruit (Citrus paradisi Macfayden)”. J. Agric. Food Chem. 47 (12): 5189—5193. PMID 10606593. doi:10.1021/jf990071l.

[4] Lehmann D.; Dietrich A.; Hener U.; Mosandl A. (1994). „Stereoisomeric flavor compounds. LXX: 1-p-menthene-8-thiol: separation and sensory evaluation of the enantiomers by enantioselective gas chromatography-olfactometry”. Phytochemical Analysis. 6 (5): 255—257. doi:10.1002/pca.2800060506.

[5] Ghose, A.K.; Viswanadhan V.N. & Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A. 102: 3762—3772. doi:10.1021/jp980230o.

[6] Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488—1493. PMID 11749573. doi:10.1021/ci000392t.

[7] Ertl P.; Rohde B.; Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

[8] Schoenauer, Sebastian; Schieberle, Peter (2016). „Structure–Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1- p -Menthene-8-thiol”. Journal of Agricultural and Food Chemistry. 64 (19): 3849—3861. PMID 27121638. doi:10.1021/acs.jafc.6b01645.

[9] Demole, E.; Enggist, P.; Ohloff, G. (1982). „1-p-Menthene-8-thiol: A powerful flavor impact constituent of grapefruit juice (Citrus parodisi MACFAYDEN)”. Helvetica Chimica Acta. 65 (6): 1785—1794. doi:10.1002/hlca.19820650614.

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