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Wax


DATA No : WWA2201 INFORMANT : Ken-ichi Tomita

NAME : Anhydrous Lanolin

COMMON NAME: Anhydrous Lanolin/Lanolin/Wool Fat (Ref. 0015) / (Ref. 0024)/ (Ref. 0059)/ (Ref. 0060) / (Ref. 0061) / (Ref. 0062) / (Ref. 0063) / (Ref. 0064) / (Ref. 0065) / (Ref. 0066) / (Ref. 0067) / (Ref. 0068) / (Ref. 0069) / (Ref. 0070) / (Ref. 0071) / (Ref. 0072) / (Ref. 0073) / (Ref. 0074) / (Ref. 0075) / (Ref. 0076)
SYMBOL:
FORMULA: Mixture MOL.WT (average) :
BIOLOGICAL ACTIVITY
Uses
Up till now lanolin has been used creams, lipsticks and other cosmtics because of its excellent affinity with the skin, adhesion and moistrizing capability as well as its very good water holding capacity and emulsion capacity.However, there have been problems with its color, odor and adhesion and, being a natural substance, its qualities may change and over time become rancid. As a result, its direct use has been decreasing in modern cosmetics. Because of this, lanolin is used as a raw material for cosmetics in different forms, made by removing some of its structural components and reacting them with other substances to produce derivatives which retain the good characteristics and overcome the problems, or substances in which the characteristics of lanolin have been enhanced. (Ref. 0015)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:Melting point 37-43degC (Ref. 0015) (Method 2) (Ref. 0001)

BOILING POINT:Iodine Value 18-36 (0.8g) (Ref. 0015)
Use chloroform and iodine monobromide TS instead of carbon tetrachloride and iodine monochloride TS, respectively. (Ref. 0005)

REFRACTIVE INDEX:Acid Value Not more than 1.0 (Ref. 0015) (Method 1, 5g) (Ref. 0003)

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:Properties
Anhydrous lanolin(Lanolin) is a semisolid oily substance which is yellowish in color and very tenacious. It has a slightlyunusal odor. It is readily soluble in ether, petroleum ether and petroleum benzene but sparingly soluble in ethanol. Though insoluble in water, lanolin absorbs around twice its volume of water. It exhibits excellent emulsification. Lanolin is not saponified by sodium hydroxide but can be saponified if heated with an alkali/ethanol solution under pressure. (Ref. 0015)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:IR Spectrum
[Spectrum 0029] (Ishiwata Katsumi Shiseido Research Center 1997 )
Infrared absorption spectrum measurement operation conditions, Equipment: Fourier transform infrared spectrophotometer FTS-40 (Biorad Co., Ltd.) , Resolution: 8 cm-1, Integration factor: 64, Wave number range: 400cm-1-4000cm-1 , Sample treatment: Potassium bromide tablets or liquid film

NMR SPECTRA:12C-NMR Spectrum
[Spectrum 0030] (Nishiya Hiroshi Shiseido Research Center 1993 )
12C-nuclear magnetic resonance spectrometry operation conditions, Equipment: JEOL-EX400 (Japan Electronics Co., Ltd. ), Standard substance: Tetramethylsilane (0.00 ppm ), Irradiation mode: 1H full irradiation, Measurement temperature: 40degC, Deuterium solvent: Deuterium chloroform

MASS SPECTRA:GC/MS Spectrum
[Spectra 0031/0032/0033/0034/0035/0036] (Kanda Kenji Shiseido Research Center 1995 )
Gas chromatograph- mass spectrometry operation conditions, Equipment: Gas chromatograph 5980 (Hewlett Packard ), Mass spectrometer: 5970 (Hewlett Packard ), Column: ULTRA ALLOY plus-1 ( HT ) ( Frontier Laboratories Ltd. ) Internal diameter: 0.25 mm, gas chromatograph capillary column joined to a 15 m long metal tube to produce a 0.15 mm thick film of dimethyl silicone as the liquid phase, Column temperature: maintain at 40degC for 3.5 minutes, then raise to 200degC at a rate of 10degC per minute, and then at 20degC per minute up to 350 degC. Maintain at this temperature for 20 minutes and then raise to 400 degC at a rate of 50 degC per minute.
Injection temperature: 320degC, Carrier gas: He, Mass range: 40-800, Split ratio: 1: 40, Sample treatment: add 100 ml N,O-Bis (trimethylsilyl) acetamide to test sample( around 5mg ) and heat at 100degC for 10 minutes, cool and make up to 1.5ml with n-hexane.

OTHER SPECTRA:
CHROMATOGRAM DATA
Gaschromatography
[Chromatograms 0011/0012] (Nakahara Kazuyoshi Shiseido Research Center 1997 )
Gas chromatography operation conditions, Equipment: Gas chromatograph 6980 ( Hewlett Packard ), Column: ULTRA ALLOY plus-1 ( HT ) ( Frontier Laboratories Ltd. ), Internal diameter: 0.50 mm, gas chromatograph capillary column joined to a 15 m long metal tube to produce a 0.50 mm thick film of dimethyl silicone as the liquid phase, Column temperature: maintain at 60 degC for 2 minutes, then raise to 370 degC at a rate of 20 degC per minute and maintain at this temperature for 12.5 minutes, Detector: FID, 380 degC, Injection temperature: 370 degC, Injection volume: 1 ml, Carrier gas: He, 33 kpa, 10ml/min. (at 40 degC ), Splitless: purge start time 2 min., Sample solution: 1 % isopentane/ pyridine ( 9:1 ) solution or 1 % isopentane solution.
SOURCE
Origin : In 1883, Liebreich and Braun succeeded in refining the substance secreted on sheep's wool, gave thisoily substance the name lanolin and took out a patent on it. Unna found out that it could be used for ointments and cosmetics, obtained a saponification product of lanolin and managed to separate lanolin alcohol from it. Lanolin is mainly a mixture of esters of higher fatty acids and higher alcohols but also contains free fatty acids, free alcohols and hydrocarbons. It thus differs chemically from the oils and fats and is classified as a wax. The fatty acid present in greatest amount is anteiso fatty acid ( CH3CH2CH( CH3)(CH2)2nCOOH (n=2-13) which comprises around 33% of the acid fraction. Next comes isofatty acid ( ( CH3)2CH(CH2)2nCOOH (n=3-12) comprising 26% of the acid fraction.
Other fatty acids include normal fatty acid ( ( CH3)( CH2)2nCOOH (n=4-12) and hydroxy fatty acid ( CH3(CH2)2n-1CH ( OH) COOH ( n=6 or 7 ). The higher alcohol present in greatest amount is sterol (mostly cholesterol) comprising 35-40% of the neutral fraction and after it comes triterpenoid sterol (mostly lanosterol ) comprising 25-30% of the neutral fraction. Aliphatic monohydric alcohol is also present. (Ref. 0015) A method of manufacture : Lanolin is produced from the secretion on sheep's wool and most of it is obtained as a by-product during the processing of sheep's wool. Broadly speaking, 4main methods are used to refine the sheep's grease, the raw material of lanolin,and all of them involve recovering it from the solution used to clean the sheep; wool. Continued to Metabolism
CHEMICAL SYNTHESIS

METABOLISM
In the first one, the grease is washed with soap and alkali and then emulsified. The emulsion is then destroyed by adding acid to obtain the lanolin. This method is mainly used in Britain. With this method, however, the lanolin contains large amounts of free fatty acids which have been hydrolyzed by the acid and this causes problems with the color and the smell. The second is known as the bubbling separation method. In this method, the solution used for cleaning the sheep's wool is aerated so that the grease collects at the top. This is then washed with water and heated to separate the grease and the water. This is the method used in Australia. In the third method, soap, alkali or a combination of soap and alkali, or a synthetic detergent is used to cleanse the sheep's wool and the emulsion of the grease (crude lanolin) thus formed is then centrifuged to obtain lanolin. This is the method primarily used in Japan and the United States.
It is an excellent method because it overcomes the problems of color and odor.With the fourth method, an organic solvent is used to extract the lanolin from the sheep's wool. With the recent strengthening of regulations on drainage, this method is now much used. As the grease obtained by the above methods contains various impurities, if required, it is refined further to produce purer lanolin. It may be filtered, treated with alkali, bleached and deodorized using activated charcoal or china clay. (Ref. 0015)
GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:The Japanese Standards of Cosmetic Ingredients Second Edition (1985) pp522-524, YAKUJI NIPPO, LTD.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0003]
AUTHOR:The Japanese Standards of Cosmetic Ingredients Second Edition (1985) pp479-480, YAKUJI NIPPO, LTD.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0005]
AUTHOR:The Japanese Standards of Cosmetic Ingredients Second Edition (1985) pp503-504, YAKUJI NIPPO, LTD.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0015]
AUTHOR:The Japanese Standards of Cosmetic Ingredients Second Edition (Annotation) I (1984) pp1238-1240, YAKUJI NIPPO, LTD.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0024]
AUTHOR:Tsuji, S., Tonogai, Y., Ito, Y., and Harada, M.
TITLE:General analysis of various natural waxes in cosmetics
JOURNAL:J. Soc. Cosmet. Chem. Jap.
VOL:192 PAGE : 79 -89 (1985)
[TOP]

[0059]
AUTHOR:Weitkamp, A. W
TITLE:The acidic constituents of Degras (wool fat, wool wax). A new method of structure elucidation.
JOURNAL:J. Am. Chem. Soc.,
VOL:67 PAGE : 447 -454 (1945)
[TOP]

[0060]
AUTHOR:Lamparczyk, Henryk, Miszkiel, Marian, Wesolowski, and Marek
TITLE:Thermoanalytical and gas chromatographic evaluation of wool wax alcohols supported by principal component analysis.
JOURNAL:Thermochim. Acta.
VOL:179 PAGE : 177 -185 (1991)
[TOP]

[0061]
AUTHOR:Lamparczyk, H., Miszkiel, M.
TITLE:Gas chromatographic evaluation of wool wax alcohols supported by principal component analysis.
JOURNAL:Chromatographia
VOL:31 PAGE : 243 -246 (1991)
[TOP]

[0062]
AUTHOR:Jourda, Mlle ; Ponchel; Moxhet, C. ; Brach, J.
TITLE:Estimation of detergent, free alcohol and cholesterol content of wool wax.
JOURNAL:Bull. Sci. Inst. Text. Fr.
VOL:1143 PAGE : 9 -23 (1982)
[TOP]

[0063]
AUTHOR:Fawaz, F., Miet, C., and Puisieux, F.
TITLE:[Analysis of ointments, oils and waxes, XIV. Composition of lanolin. 3. Study of the hydroxylated acids of total lanolin and its various fractions] PubMed ID:4441000
JOURNAL:Ann Pharm Fr.
VOL:32 PAGE : 59-68 (1974)
[TOP]

[0064]
AUTHOR:Fawaz, F., Chaigneau, M., and Puisieux, F.
TITLE:[Analysis of ointments, oils and waxes. XV. -- Chemical composition of lanolin. 4. The aliphatic alcohols of total lanoline and its different fractions] PubMed ID:4433122
JOURNAL:Ann Pharm Fr.
VOL:32 PAGE : 215-225 (1974)
[TOP]

[0065]
AUTHOR:Modrzejewski, Feliks; Kwiatkowska, Maria
TITLE:Thin layer chromatography of steroids from lanolin
JOURNAL:Ann. Acad. Med. Lodz
VOL:12 PAGE : 373 -377 (1971)
[TOP]

[0066]
AUTHOR:Modi, Giuseppe; Simiani, Giuliano
TITLE:Determination of cholesterol and lanosterol in lanolin
JOURNAL:Boll. Lab. Chim. Prov.
VOL:222 PAGE : 151 -167 (1971)
[TOP]

[0067]
AUTHOR:Zelenetskaya, A. A. ; Glukhova, O. L.
TITLE:Chromatographic determination of hydrocarbons in lanolin and wool fat.
JOURNAL:Maslo-Zhir. Prom
VOL:367 PAGE : 33 -34 (1970)
[TOP]

[0068]
AUTHOR:Fawaz ; Chaigneau, Marcel; Giry, Lucien; Puisieux, Francis
TITLE:Mass spectrometry study of lanolin hydrocarbons
JOURNAL:C.R. Acad. Sci., Ser. C
VOL:270 PAGE : 1577 -1880 (1970)
[TOP]

[0069]
AUTHOR:Clark E. W.
TITLE:Estimation of the general incidence of specific lanolin allergy.
JOURNAL:J. Soc. Cosmet., Chemist's of Great Britain
VOL:267 PAGE : 323 -335 (1975)
[TOP]

[0070]
AUTHOR:Clark E. W.
TITLE:Estimation of the general incidence of specific lanolin allergy.
JOURNAL:Cosmetic & Toiletries
VOL:916 PAGE : 12 -14 (1976)
[TOP]

[0071]
AUTHOR:Mortensen, T.
TITLE:Allergy to lanolin PubMed ID:455960
JOURNAL:Contact Dermatitis.
VOL:5 PAGE : 137-139 (1979)
[TOP]

[0072]
AUTHOR:Sato, Y., and Kobayashi, T.
TITLE:[Allergenicity of lanolin in guinea pig assay] PubMed ID:7171316
JOURNAL:Arerugi.
VOL:31 PAGE : 1205-1214 (1982)
[TOP]

[0073]
AUTHOR:Kozuka T.
TITLE:Contact dermatitis of lanolin.
JOURNAL:Medicine & Drug Journal
VOL:1241 PAGE : 171 -177 (1976)
[TOP]

[0074]
AUTHOR:Kozuka T. et al
TITLE:Contact dermatitis of lanolin
JOURNAL:Skin Rsearch
VOL:181 PAGE : 35 -37 (1976)
[TOP]

[0075]
AUTHOR:Sugai, T. et al
TITLE:The actual condition of lanolin hypersensitivity
JOURNAL:Skin Research
VOL:202 PAGE : 239 - (1978)
[TOP]

[0076]
AUTHOR:Velluz L, Lederer E
TITLE:Sur les constituants de la graisse de laine. I. Essai de mise au point de la question jusqu'a ce jour,
JOURNAL:Bull. Soc. Chim. Biol.,
VOL:27 PAGE : 211 - (1945)
[TOP]

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