Whale, sperm

Spermaceti is a wax obtained from the sperm whale It contains among other materials an ester known as cetyl palmitate which is used as an emollient in a number of soaps and cosmetics The systematic name for cetyl palmi tate IS hexadecyl hexadecanoate Write a structural formula for this substance... 

Fats and oils are one of the oldest classes of chemical compounds used by humans. Animal fats were prized for edibiUty, candles, lamp oils, and conversion to soap. Fats and oils are composed primarily of triglycerides (1), esters of glycerol and fatty acids. However, some oils such as sperm whale (1), jojoba (2), and orange roughy (3) are largely composed of wax esters (2). Waxes (qv) are esters of fatty acids with long-chain aUphatic alcohols, sterols, tocopherols, or similar materials. 

With the beginning of the industrial revolution around 1800, oil became increasingly important for lubrication and better illumination. Expensive vegetable oils were replaced by sperm whale oil [8002-24-2], which soon became scarce and its price skyrocketed. In 1850 lubrication oil was extracted from coal and oil shale (qv) in England, and ultimately about 130 plants in Great Britain and 64 plants in Pennsylvania, West Virginia, and Kentucky employed this process. 

Spermaceti. Spermaceti [8002-23-1] is derived from the head oil of the sperm whale. Owing to the present status of the sperm whale as an endangered species, however, the material is no longer an item of commerce and has been replaced by other natural and synthetic waxes. 

Jojoba is a desert crop that gives a small bean containing about 50% of a wax, a fatty acid ester with a fatty alcohol. The only other large source of such a wax is sperm whale oil, traditionally used in fine lubricants (see Lubrication and lubricants). Because the sperm whale is an endangered species, relatively Httle sperm whale oil is available and there is a large market for a substitute. Jojoba oil has been found to be usable for most of these appHcations. The jojoba oil is obtained by simply pressing the nut followed by conventional refining. Some jojoba oil is used in cosmetics (qv). 

Myoglobin (from sperm whale muscle). [9047-17-0] M, -17,000. Purified by CM-cellulose chromatography and Sephadex G-50 followed by chromatography on Amberlite IRC-50 Type III or BioRex 70 (<400mesh). The crystalline product as a paste in saturated (NH4)2S04 at pH 6.5-7.0 may be stored at 4° for at least 4 years unchanged, but must not be kept in a freezer. [Anres and Atassi Biochemistry 12 942 1980, Edmundson Biochem Prep 12 41 1968.]... 

Spermaceti is a wax obtained from the sperm whale. It contains. 

Mb Sperm whale myoglobin, an oxygen-binding protein 153 amino acid residues. Note that Mb lacks cysteine. 

Both attractive forces and repulsive forces are included in van der Waals interactions. The attractive forces are due primarily to instantaneous dipole-induced dipole interactions that arise because of fluctuations in the electron charge distributions of adjacent nonbonded atoms. Individual van der Waals interactions are weak ones (with stabilization energies of 4.0 to 1.2 kj/mol), but many such interactions occur in a typical protein, and, by sheer force of numbers, they can represent a significant contribution to the stability of a protein. Peter Privalov and George Makhatadze have shown that, for pancreatic ribonuclease A, hen egg white lysozyme, horse heart cytochrome c, and sperm whale myoglobin, van der Waals interactions between tightly packed groups in the interior of the protein are a major contribution to protein stability. 

When oil from the head of the sperm whale is cooled, spermaceti, a translucent wax with a white, pearly luster, crystallizes from the mixture. Spermaceti, which makes up 11% of whale oil, is composed mainly of the wax cetyl pabnitate ... 

FIGURE 15.23 The myoglobin and hemoglobin molecules. Myoglobin (sperm whale) one polypeptide chain of 153 aa residues (mass = 17.2 kD) has one heme (mass = 652 D) and binds one O9. Hemoglobin (human) four polypeptide chains, two of 141 aa residues (u) and two of 146 residues (/3) mass = 64.45 kD. Each polypeptide has a heme the Hb tetramer binds four O9. (Irving Geis)... 

Spermaceti, a fragrant substance from sperm whales, was much used in cosmetics until it was banned in 1976 to protect the whales from extinction. Chemically, spermaceti is cetyl palmitate, the ester of cetyl alcohol (u-ClrtH33OH) with palmitic acid. Draw its structure. 

Shire, SJ Hanania, GIH Gurd, FRN, Electrostatic Effects in Myoglobin. Hydrogen Ion Equilibria in Sperm Whale Ferrimyoglobin, Biochemistry 13, 2967, 1974. 

Ambergris 53-83 Intestines of sperm whale Perfume, cosmetic... 

Spermaceti 43—47 Head cavity of sperm whale Making candles, leather and textiles dressing... 

Spermaceti Extracted from head cavities of sperm whales Even numbered esters (C26 C36)... 

J.F. Stargardt, F.M. Fiawkridge, and H.L. Landrum, Reversible heterogeneous reduction and oxidation of sperm whale myoglobin at a surface modified gold minigrid electrode. Anal. Chem. 50, 930-932 (1978). 

Pygmy sperm whale, Kogia brevicepsr, Argentina found dead ... 

Sperm whale Physeter macrocephalus southern Australia 1976 muscle... 

Cannella, E.G. and D.J. Kitchener. 1992. Differences in mercury levels in female sperm whale, Physeter macrocephalus (Cetacea Odontoceti). Austral. Mammal. 15 121-123. 

Law, R.J., R.L. Stringer, C.R. Allchin, and B.R. Jones. 1996. Metals and organochlorines in sperm whales (Physeter macrocephalus) stranded around the North Sea during the 1994/1995 winter. Mar. Pollut. Bull. 32 72-77. 

Sperm whale, Physeter macrocephalus] Alaska, 1965, bone vs. soft tissue ... 

Tooth and tusk ivory can be carved into an almost infinite variety of shapes and objects. A small example of carved ivory objects are small (50) statuary, netsukes, jewelry, flatware handles, furniture inlays, and piano keys. Additionally, wart hog tusks, and teeth from sperm whales, killer whales, and hippos can also be scrimshawed or superficially carved, thus retaining their original shapes as morphologically recognizable objects. 

Figure 13.5 (a) The structure of sperm whale myoglobin. (From Voet and Voet, 2004. Reproduced with permission from John Wiley Sons., Inc.) (b) The oxygen-binding curves of myoglobin and haemoglobin. (Reprinted with permission from Collman et al., 2004. Copyright (2004) American Chemical Society.)... 

J. A. Westrick, J. L. Goodman, K. S. Peters. A Time-Resolved Photoacoustic Calorimetry Study of the Dynamics of Enthalpy and Volume Changes Produced in the Photodissociation of Carbon Monoxide from Sperm Whale Carboxymyoglobin. Biochemistry 1987, 26, 8313-8318. 

Figure 12.2 Structure of waxes. The general structure of a wax is shown in which n and m are usually between 8 and 18. The structure of hexadecyl hexadecanoate (cetyl palmitate), a wax found in sperm whale oil, is shown. This is an ester of hexadecanoic (palmitic) acid and hexadecanol (cetyl alcohol).

Bismuto et alF compared the phosphorescence from both tuna and sperm whale apomyoglobin. The emission occurs from a tryptophan in the A helix. The temperature dependence of lifetime and the position of the 0-0 vibrational band differ as a function of temperature for the two proteins. The authors interpreted their results to indicate that the microenvironment of the tryptophan in sperm whale apomyoglobin possesses a higher degree of internal flexibility than that in the tuna protein. 

Fig. 3. Electron density contours of sperm whale myoglobin at 6 A resolution.

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