Remedy/Alcohols

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International Union of Pure and Applied Chemistry (IUPAC) nomenclature in naming simple alcohols, the name of the alkane chain loses the terminal e and adds the suffix -ol, e.g., as in "ethanol" from the alkane chain name "ethane".[1] When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the -ol: propan-1-ol for CH
3
CH
2
CH
2
OH
, isopropyl alcohol (propan-2-ol) for CH
3
CH(OH)CH
3
. If a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), then the prefix hydroxy-is used,[1] e.g., as in 1-hydroxy-2-propanone (CH
3
C(O)CH
2
OH
).[2]

Simple alcohols[edit | edit source]

Some examples of simple alcohols and how to name them
CH
3
CH
2
CH
2
–OH
Propan-2-ol displayed.svg Cyclohexanol displayed.svg 2-methylpropan-1-ol displayed.svg 2-methylbutan-2-ol displayed.svg
Propan-1-ol.svg 2-Propanol.svg Cyclohexanol acsv.svg Isobutanol.svg 2-Methyl-2-butanol FormulaV1-Seite001.svg
n-propyl alcohol,
propan-1-ol, or
1-propanol
isopropyl alcohol,
propan-2-ol, or
2-propanol
cyclohexanol isobutyl alcohol,
2-methylpropan-1-ol, or
2-methyl-1-propanol
tert-amyl alcohol,
2-methylbutan-2-ol, or
2-methyl-2-butanol
A primary alcohol A secondary alcohol A secondary alcohol A primary alcohol A tertiary alcohol

In cases where the OH functional group is bonded to an sp2 carbon on an aromatic compound (aromatic ring) the molecule is known as a phenol, and is named using the IUPAC rules for naming phenols.[3]

Type Formula IUPAC Name Common name
Monohydric
alcohols
CH
3
OH
Methanol Wood alcohol
C
2
H
5
OH
Ethanol Alcohol
C
3
H
7
OH
Propan-2-ol Isopropyl alcohol,
Rubbing alcohol
C
4
H
9
OH
Butan-1-ol Butanol,
Butyl alcohol
C
5
H
11
OH
Pentan-1-ol Pentanol,
Amyl alcohol
C
16
H
33
OH
Hexadecan-1-ol Cetyl alcohol
Polyhydric
alcohols
C
2
H
4
(OH)
2
Ethane-1,2-diol Ethylene glycol
C
3
H
6
(OH)
2
Propane-1,2-diol Propylene glycol
C
3
H
5
(OH)
3
Propane-1,2,3-triol Glycerol
C
4
H
6
(OH)
4
Butane-1,2,3,4-tetraol Erythritol,
Threitol
C
5
H
7
(OH)
5
Pentane-1,2,3,4,5-pentol Xylitol
C
6
H
8
(OH)
6
hexane-1,2,3,4,5,6-hexol Mannitol,
Sorbitol
C
7
H
9
(OH)
7
Heptane-1,2,3,4,5,6,7-heptol Volemitol
Unsaturated
aliphatic
alcohols
C
3
H
5
OH
Prop-2-ene-1-ol Allyl alcohol
C
10
H
17
OH
3,7-Dimethylocta-2,6-dien-1-ol Geraniol
C
3
H
3
OH
Prop-2-yn-1-ol Propargyl alcohol
Alicyclic
alcohols
C
6
H
6
(OH)
6
Cyclohexane-1,2,3,4,5,6-hexol Inositol
C
10
H
19
OH
5-Methyl-2-(propan-2-yl)cyclohexan-1-ol Menthol

Polycosanols[edit | edit source]

Diagram shows oleyl alcohol. Credit: .{{free media}}
Diagram shows 1-octacosanol. Credit: Benrr101.{{free media}}
Diagram shows 1-nonacosanol. Credit: .{{free media}}
Chemical structure shows 1-dotriacontanol. Credit: Edgar181.{{free media}}

Def. an "extract of plant waxes, rich in long-chain aliphatic alcohols"[4] is called a polycosanol, or policosanol.

Policosanol was originally derived from sugar cane but the chemicals can also be isolated from beeswax, cereal grains, grasses, leaves, fruits, nuts, and seeds of many foods.[5] Policosanols are very long chain alcohols with carbon backbones ranging from 24 to 34 carbons.[5]

The first policosanol supplements were produced by Dalmer Laboratories in Cuba; studies conducted and published by that group have found that policosanol is safe and effective as a lipid-lowering agent; however these studies were small, and efforts by groups outside of Cuba have failed to replicate these results.[5]

A meta-analysis in 2005 concluded that human policosanol consumption is safe and well tolerated and is effective at lowering the blood cholesterol.[6] As of 2010, they were marketed as lipid-lowering agents in the Caribbean, Central and South America, and Canada.[5] Furthermore, another meta-analysis was published in 2018 with 22 studies and 1886 subjects showed policosanol could improve dyslipidemia with raising HDL.[7] The blood pressure lowering effect of Cuban policosanol has been shown in an animal model using spontaneously hypertensive rats (SHR)[8] and a human trial.[9][10]

"Weighted estimates of percent change in LDL were -11.0% for plant sterol and stanol esters 3.4 g/day (range 2-9 g/day [893 patients]) versus -2.3% for placebo (769 patients) in 23 eligible studies, compared with -23.7% for policosanol 12 mg/day (range 5-40 mg/day [1528 patients]) versus -0.11% for placebo (1406 patients) in 29 eligible studies."[6]

A "nutraceutical combination (NC), consisting of 500 mg berberine, 200 mg red yeast rice and 10 mg policosanols, on cholesterol levels and endothelial function in patients with hypercholesterolemia [produced] a main outcome measure was decrease total cholesterol (C) levels in the NC arm. Secondary outcome measures were decreased low-density lipoprotein cholesterol (LDL-C) and triglyceride levels, and improved endothelial-dependent flow-mediated dilation (FMD) and insulin sensitivity in relation to NC. Evaluation of absolute changes from baseline showed significant reductions in NC versus placebo for C and LDL-C (C: −1.14 ± 0.88 and −0.03 ± 0.78 mmol/l, p < 0.001; LDL-C: −1.06 ± 0.75 and −00.4 ± 0.54 mmol/l, p < 0.001), and a significant improvement of FMD (3 ± 4% and 0 ± 3% respectively, p < 0.05). After the extension phase, triglyceride levels decreased significantly from 1.57 ± 0.77 to 1.26 ± 0.63 mmol/l, p < 0.05 and insulin sensitivity improved in a patient subgroup with insulin resistance at baseline (HOMA: from 3.3 ± 0.4 to 2.5 ± 1.3, p < 0.05)."[11]

"Policosanol (10 mg/day) significantly reduced total cholesterol by 17.5% and LDL cholesterol by 21.8% compared with baseline and placebo. Furthermore, high-density lipoprotein (HDL) cholesterol was raised by 11.3% (not significant), and triglycerides showed a statistically nonsignificant decrease of 6.6%. These changes in lipid profile were similar to those induced by policosanol in nondiabetic patients with type II hyperlipoproteinemia."[12]

"At 4 (p < 0.0001) and 8 (p < 0.00001) weeks, policosanol 10 mg/day significantly lowered serum LDL-C levels by 17.5 and 23.1%, respectively compared with baseline; corresponding values for atorvastatin were 28.4 and 29.8%. At study completion, policosanol significantly (p < 0.0001) reduced serum TC (16.4%), LDL-C/HDL-C ratio (25.5%) and TC/HDL-C ratio (19.3%), as well as (p < 0.001) triglyceride levels (15.4%). Atorvastatin significantly (p < 0.0001) decreased serum TC (22.6%), LDL-C/HDL-C (26.2%) and TC/HDL-C (19.8%) ratios, as well as (p < 0.001) triglyceride levels (15.5%). Atorvastatin was significantly more effective than policosanol in reducing LDL-C and TC, but similar in reducing both atherogenic ratios and triglyceride levels. Policosanol, but not atorvastatin, significantly (p < 0.05) increased serum HDL-C levels by 5.3%. Both treatments were well tolerated. At study completion, atorvastatin mildly, but significantly (p < 0.05) increased creatine phosphokinase (CPK) and creati-nine, whereas policosanol significantly reduced AST and glucose (p < 0.01) and CPK (p < 0.05) levels. All individual values, however, remained within normal limits. Three atorvastatin but no policosanol patients withdrew from the study because of adverse events: muscle cramps (1 patient), gastritis (1 patient) and uncontrolled hypertension, abdominal pain and myalgia (1 patient). Overall, no policosanol and seven atorvastatin patients (18.9%) reported a total of nine mild or moderate adverse events during the study (p < 0.01)."[13]

"Fifty-three elderly patients (60 to 77 years of age) with primary hypercholesterolemia (total serum cholesterol ⩾240 mg/dL) were enrolled in a randomized, double-masked, parallel-group, comparative study of policosanol—a new cholesterol-lowering agent obtained from sugarcane wax—and simvastatin. Before randomization, all patients were advised to follow a standard cholesterol-lowering diet for 6 weeks. Patients were randomized to receive either policosanol or simvastatin, both at doses of 10 mg/d for 8 weeks. With policosanol, total cholesterol, low-density lipoprotein cholesterol (LDL-C), and triglycerides were significantly reduced 14.7%, 17.9%, and 13.8%, respectively. Simvastatin significantly lowered total cholesterol 15.2%, LDL-C 19.8%, and triglycerides 8.7%. Neither policosanol nor simvastatin significantly changed high-density lipoprotein cholesterol (HDL-C) levels. Total cholesterol:HDL-C and LDL-C:HDL-C ratios were significantly lowered by both therapies. The effects of both drugs on lipid profile variables were statistically similar. Both drugs were well tolerated."[14]

"After 5 weeks of a standard step-1 lipid-lowering diet, 437 patients were randomized to receive, under double-blind conditions, 5 mg policosanol or placebo once a day with the evening meal for 12 weeks and 10 mg policosanol or placebo for the next 12 weeks."[15]

"Both groups were similar at randomization. Policosanol (5 and 10 mg/day) significantly reduced (P < .001) serum low-density lipoprotein cholesterol (18.2% and 25.6%, respectively) and cholesterol (13.0% and 17.4%), and it significantly raised (P < .01) high-density lipoprotein cholesterol (15.5% and 28.4%). Triglycerides remained unchanged after the first 12 weeks and lowered significantly (5.2%; P < .01) at study completion. Policosanol was safe and well tolerated, and no drug-related disturbances were observed. Two male patients who received placebo died during the study—one because of a myocardial infarction and the other because of a cardiac arrest that occurred during a surgical intervention. There were 11 serious adverse events (5.1%) in 10 patients who received placebo (4.6%), 7 of which were vascular, compared with no serious adverse events reported in patients receiving policosanol (P < .01)."[15]

Fatty alcohols (or long-chain alcohols), usually high-molecular-weight, straight-chain primary alcohols, can range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils, where the precise chain length varies with the source.[16][17]

"Policosanol is a mixture of alcohols isolated and purified from sugar cane (Saccharum officinarum L). It consists mainly of 66-percent octacosanol (C
28
H
58
O
), 12-percent triacontanol, and 7-percent hexacosanol. Other alcohols (15%), namely tetracosanol, heptacosanol, nonacosanol, dotriacontanol and tetratriacontanol, are minor components.(1)"[18]

Dodecanol, or lauryl alcohol, an organic compound (C12H26O) produced industrially from palm kernel oil or coconut oil, a fatty alcohol is tasteless and colorless with a floral odor.[19]

Oleyl alcohol,[20] or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C
18
H
36
O
or the condensed structural formula CH3(CH2)7-CH=CH-(CH2)8OH. It is a colorless oil, mainly used in cosmetics.[16]

Stearyl alcohol, or 1-octadecanol, an organic compound classified as a saturated fatty alcohol with the formula CH3(CH2)16CH2OH (C18H38O), application as an evaporation suppressing monolayer when applied to the surface of water.[21]

1-Tetracosanol (lignoceryl alcohol) is a fatty alcohol containing 24 carbon atoms C
24
H
50
O
, usually derived from the fatty acid lignoceric acid.

1-Hexacosanol a saturated primary fatty alcohol with a carbon chain length of 26 (C
26
H
54
O
) that is a white waxy solid at room temperature, occurs naturally in the epicuticular wax and plant cuticle of many plant species.[22]

1-Heptacosanol is a fatty alcohol with the formula C
27
H
56
O
.

1-Octacosanol (also known as n-octacosanol, octacosyl alcohol, cluytyl alcohol, montanyl alcohol) is a straight-chain aliphatic 28-carbon primary fatty alcohol (C
28
H
58
O
) that is common in the epicuticular waxes of plants, including the leaves of many species of Eucalyptus, of most forage and cereal grasses, of Acacia, Trifolium, Pisum and many other legume genera among many others, sometimes as the major wax constituent.[22] Octacosanol also occurs in wheat germ.[23]

Octacosanol is the main component in the mixture policosanol.[24] Octacosanol has been subject to preliminary study for its potential benefit for patients with Parkinson's disease.[25][26] Studies have also found that octacosanol may inhibit the production of cholesterol.[24] In mice, octacosanol reduces stress and restores stress-affected sleep back to normal.[27]

"Daily doses of 10 mg of policosanol have been shown to be equally effective in lowering total or LDL cholesterol as the same dose of simvastatin or pravastatin. Triglyceride levels are not influenced by policosanol."[28]

1-Nonacosanol is a straight-chain aliphatic 29-carbon primary fatty alcohol with the formula C
29
H
60
O
.

1-Triacontanol (n-triacontanol) is a fatty alcohol of the general formula C
30
H
62
O
, also known as melissyl alcohol or myricyl alcohol, found in plant cuticle waxes and in beeswax, a growth stimulant for many plants, most notably roses, in which it rapidly increases the number of basal breaks, a natural plant growth regulator, widely used to enhance the yield of various crops around the world, mainly in Asia.[29]

Triacontanol was first isolated in 1933 from alfalfa, identified as a saturated straight chain primary alcohol.[30] Triacontanol is found in various plant species as a minor component of the epicuticular wax, in wheat, triacontanol is about 3-4% of the leaf wax.[31] A substantial increase in yield and growth has been seen in different plants, such as cucumber, tomatoes, wheat, maize, lettuce, and rice.[32]

1-Dotriacontanol is a fatty alcohol with 32 carbon atoms for a chemical formula C
32
H
66
O
.

Geddic acid, or tetratriacontanoic acid, is a 34-carbon-long carboxylic acid and saturated fatty acid that occurs in cotton, carnauba, candelilla wax and in ghedda wax (wild beeswax), from which its common name is derived with the formula C
34
H
68
O
2
. Tetratriacontanol has the chemical formula C
34
H
70
O
.

"The total [polycosanol] PC contents of wheat straw (164 mg/kg) and sugar cane peel (270 mg/kg) were of the same order of magnitude. The total PC contents of brown beeswax were about 20 and 45 times higher than those of the [wheat germ oil] WGO-solids and sugar cane peel, respectively. Commercial dietary supplements contained less total PC than were claimed on the product labels."[33]

See also[edit | edit source]

References[edit | edit source]

  1. 1.0 1.1 William Reusch (19 September 2007). "Alcohols". VirtualText of Organic Chemistry.
  2. Organic chemistry IUPAC nomenclature. Alcohols Rule C-201.
  3. Organic Chemistry Nomenclature Rule C-203: Phenols
  4. SemperBlotto (14 April 2009). "polycosanol". San Francisco, California: Wikimedia Foundation, Inc. Retrieved 26 June 2021.
  5. 5.0 5.1 5.2 5.3 "Policosanols as nutraceuticals: fact or fiction". Critical Reviews in Food Science and Nutrition 50 (3): 259–67. March 2010. doi:10.1080/10408391003626249. PMID 20301014. 
  6. 6.0 6.1 Judy T Chen, Robert Wesley, Robert D Shamburek, Frank Pucino, Gyorgy Csako (February 2005). "Meta-analysis of natural therapies for hyperlipidemia: plant sterols and stanols versus policosanol". Pharmacotherapy 25 (2): 171-83. doi:10.1592/phco.25.2.171.56942. PMID 15767233. https://pubmed.ncbi.nlm.nih.gov/15767233/. Retrieved 8 July 2021. 
  7. Gong, Jing; Qin, Xin; Yuan, Fen; Hu, Meilin; Chen, Guang; Fang, Ke; Wang, Dingkun; Jiang, Shujun et al. (2018). "Efficacy and safety of sugarcane policosanol on dyslipidemia: A meta-analysis of randomized controlled trials". Molecular Nutrition & Food Research 62 (1): 1700280. doi:10.1002/mnfr.201700280. PMID 28730734. 
  8. Cho KH, Yadav D, Kim SJ, Kim JR (May 2018). "Blood Pressure Lowering Effect of Cuban Policosanol is Accompanied by Improvement of Hepatic Inflammation, Lipoprotein Profile, and HDL Quality in Spontaneously Hypertensive Rats". Molecules 23 (5): 1080. doi:10.3390/molecules23051080. PMID 29751583. PMC 6102548. //www.ncbi.nlm.nih.gov/pmc/articles/PMC6102548/. 
  9. "Consumption of Cuban Policosanol Improves Blood Pressure and Lipid Profile via Enhancement of HDL Functionality in Healthy Women Subjects: Randomized, Double-Blinded, and Placebo-Controlled Study". Oxidative Medicine and Cellular Longevity 2018: 1–15. 2018. doi:10.1155/2018/4809525. PMID 29854085. 
  10. "Long-Term Consumption of Cuban Policosanol Lowers Central and Brachial Blood Pressure and Improves Lipid Profile With Enhancement of Lipoprotein Properties in Healthy Korean Participants". Frontiers in Physiology 9: 412. 2018. doi:10.3389/fphys.2018.00412. PMID 29765328. 
  11. F. Affuso, A. Ruvolo, F. Micillo, L. Saccà, S. Fazio (November 2010). "Effects of a nutraceutical combination (berberine, red yeast rice and policosanols) on lipid levels and endothelial function randomized, double-blind, placebo-controlled study". Nutrition, Metabolism and Cardiovascular Diseases 20 (9): 656-661. https://www.sciencedirect.com/science/article/abs/pii/S0939475309001392. Retrieved 8 July 2021. 
  12. Omayda Torres, A J Agramonte, Jose Illnait, Rosa Más Ferreiro, Lilia Fernández, and Julio C Fernández (March 1995). "Treatment of Hypercholesterolemia in NIDDM With Policosanol". Diabetes Care 18 (3): 393-397. doi:10.2337/diacare.18.3.393. https://care.diabetesjournals.org/content/18/3/393.short. Retrieved 8 July 2021. 
  13. Gladys Castaño, Rosa Mas, Lilia Fernández, José Illnait, Meylin Mesa, Estrella Alvarez & Magnolia Lezcay (February 2003). "Comparison of the Efficacy and Tolerability of Policosanol with Atorvastatin in Elderly Patients with Type II Hypercholesterolaemia". Drugs & Aging 20: 153–163. doi:10.2165/00002512-200320020-00006. https://link.springer.com/article/10.2165/00002512-200320020-00006. Retrieved 8 July 2021. 
  14. Graciela Ortensi, Julio Gladstein, Hector Valli and Pedro A. Tesone (June 1997). "A comparative study of policosanol versus simvastatin in elderly patients with hypercholesterolemia". Current Therapeutic Research 58 (6): 390-401. doi:10.1016/S0011-393X(97)80099-9. https://www.sciencedirect.com/science/article/abs/pii/S0011393X97800999. Retrieved 8 July 2021. 
  15. 15.0 15.1 Rosa Más, Gladys Castaño, José Illnait, Lilia Fernández, Julio Fernández, Celia Alemán, Virginia Pontigas, Magnolia Lescay (5 April 1999). "Effects of policosanol in patients with type II hypercholesterolemia and additional coronary risk factors". Clinical Pharmacology & Therapeutics 65 (4): 439-447. doi:10.1016/S0009-9236(99)70139-6. https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/S0009-9236(99)70139-6. Retrieved 8 July 2021. 
  16. 16.0 16.1 Noweck, Klaus; Grafahrend, Wolfgang. "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2.
  17. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "Molecule". doi:10.1351/goldbook.M04002 "Fatty alcohol"
  18. Mark Janikula (June 2002). "Policosanol: a new treatment for cardiovascular disease?". Alternative Medicine Review 7 (3): 203. https://go.gale.com/ps/i.do?id=GALE%7CA88823870&sid=googleScholar&v=2.1&it=r&linkaccess=abs&issn=10895159&p=AONE&sw=w&userGroupName=anon%7Ed10784f8. Retrieved 8 July 2021. 
  19. Ford, S. G.; Marvel, C. S. (1930). "Lauryl Alcohol". Organic Syntheses 10: 62. doi:10.15227/orgsyn.010.0062. 
  20. "Oleyl" in the McGraw–Hill Dictionary of Scientific & Technical Terms (2003)
  21. Prime, E. L., Tran, D. N., Plazzer, M., Sunartio, D., Leung, A. H., Yiapanis, G., ... & Solomon, D. H. (2012). Rational design of monolayers for improved water evaporation mitigation. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 415, 47-58.
  22. 22.0 22.1 EA Baker (1982) Chemistry and morphology of plant epicuticular waxes. pp. 139–165. In "The Plant Cuticle". edited by DF Cutler, KL Alvin and CE Price. Academic Press, London. isbn=0-12-199920-3
  23. "Octacosanol". Natural Products (Professional). drugs.com. Archived from the original on 3 June 2009. Retrieved 9 July 2009. isolated from wheat germ oil or other plants
  24. 24.0 24.1 Taylor, Johanna C; Rapport, Lisa; Lockwood, G.Brian (2003). "Octacosanol in human health". Nutrition 19 (2): 192–5. doi:10.1016/S0899-9007(02)00869-9. PMID 12591561. 
  25. Snider, SR (1984). "Octacosanol in parkinsonism". Annals of Neurology 16 (6): 723. doi:10.1002/ana.410160615. PMID 6395790. 
  26. Wang, T; Liu, YY; Wang, X; Yang, N; Zhu, HB; Zuo, PP (2010). "Protective effects of octacosanol on 6-hydroxydopamine-induced Parkinsonism in rats via regulation of ProNGF and NGF signaling". Acta Pharmacologica Sinica 31 (7): 765–74. doi:10.1038/aps.2010.69. PMID 20581854. 
  27. Kaushik, MK; Aritake, K; Takeuchi, A; Yanagisawa, M; Urade, Y (21 August 2017). "Octacosanol restores stress-affected sleep in mice by alleviating stress". Scientific Reports 7 (1): 8892. doi:10.1038/s41598-017-08874-2. PMID 28827687. 
  28. Ioanna Gouni-Berthold and Heiner K.Berthold (February 2002). "Policosanol: clinical pharmacology and therapeutic significance of a new lipid-lowering agent". American Heart Journal 143 (2): 356-365. doi:10.1067/mhj.2002.119997. http://img2.timg.co.il/forums/64382387.doc. Retrieved 8 July 2021. 
  29. Naeem, M.; Khan, M. Masroor A.; Moinuddin (2012). "Triacontanol: A potent plant growth regulator in agriculture". Journal of Plant Interactions 7 (2): 129–142. doi:10.1080/17429145.2011.619281. 
  30. Chibnall, A.C., E.F. Williams, A.L, Latner, and S.H. Piper (1933). "The isolation of n-triacontanol from lucerne wax". Biochemical Journal 27 (6): 1885–1888. doi:10.1042/bj0271885. PMID 16745314. 
  31. Tulloch, A.P., and L.L., Hoffman. 1974. Epicuticular wax of Secale cereale and Triticale hexaploide leaves. Phytochemistry 13: 2535-2540.
  32. Ries, S.K., H. Bittenbinder, R. Hangarter, L.Kolker, G. Morris, and V. Wert. 1976. Improved Growth and Yield of crops from organic supplements. Pages 377-384 in W. Lokeretz, ed. Energy and Agriculture. Academic Press, New York.
  33. Sibel Irmak, Nurhan Turgut Dunford and Jeff Milligan (March 2006). "Policosanol contents of beeswax, sugar cane and wheat extracts". Food Chemistry 95 (2): 312-318. doi:10.1016/j.foodchem.2005.01.009. https://www.sciencedirect.com/science/article/abs/pii/S0308814605000816. Retrieved 15 July 2021. 

Further reading[edit | edit source]

External links[edit | edit source]