Knowledge (XXG)

Lipophilicity

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130:(lowering interfacial tension). At these surfaces they naturally orient themselves with their head groups in water and their tails either sticking up and largely out of water (as at the air-water interface) or dissolved in the water-immiscible phase that the water is in contact with (e.g. as the emulsified oil droplet). In both these configurations the head groups strongly interact with water while the tails avoid all contact with water. Surfactant molecules also aggregate in water as 138:
draw oily substances into their hydrophobic cores, explaining the basic action of soaps and detergents used for personal cleanliness and for laundering clothes. Micelles are also biologically important for the transport of fatty substances in the small intestine surface in the first step that leads
122:(or amphipathic), having a hydrophilic, water interactive "end", referred to as their "head group", and a lipophilic "end", usually a long chain hydrocarbon fragment, referred to as their "tail". They congregate at low energy surfaces, including the air-water interface (lowering 167:, a common cosmetic ingredient often used in sunscreens, penetrates the skin particularly well because it is not very lipophilic. Anywhere from 0.4% to 8.7% of oxybenzone can be absorbed after one topical sunscreen application, as measured in urine excretions. 80:(translated as "fat-loving" or "fat-liking"). Such non-polar solvents are themselves lipophilic, and the adage "like dissolves like" generally holds true. Thus lipophilic substances tend to dissolve in other lipophilic substances, whereas 276:
H. Gonzalez, H., Farbrot, A., Larko. O., and Wennberg, A. M. (2006). "Percutaneous absorption of the sunscreen benzophenone-3 after repeated whole-body applications, with and without ultraviolet irradiation".
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Hanson KM, Gratton E, Bardeen CJ. (2006). "Sunscreen enhancement of UV-induced reactive oxygen species in the skin".
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Lipophilicity, hydrophobicity, and non-polarity may describe the same tendency towards participation in the
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to the absorption of the components of fats (largely fatty acids and 2-monoglycerides).
84:("water-loving") substances tend to dissolve in water and other hydrophilic substances. 586: 541: 531: 448: 343: 333: 233: 92: 41: 661: 468: 428: 373: 196: 191: 143: 100: 28: 91:, as the terms are often used interchangeably. However, the terms "lipophilic" and " 488: 483: 641: 556: 119: 115: 111: 81: 636: 626: 621: 498: 164: 158: 646: 601: 516: 147: 127: 17: 463: 135: 131: 96: 218: 566: 368: 358: 126:) and the surfaces of the water-immiscible droplets found in oil/water 73: 134:
with their head groups sticking out and their tails bunched together.
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Affinity of a molecule or a moiety for a lipophilic environment
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Cell membranes are bilayer structures principally formed from
57: 53: 146:, molecules which have a highly water interactive, ionic 27:"Lipophilia" redirects here. For the paraphilia, see 607:
List of boiling and freezing information of solvents
565: 497: 427: 324: 232: 150:head groups attached to two long alkyl tails. 302: 8: 103:, which are hydrophobic but not lipophilic. 309: 295: 287: 161:because fluorocarbons are not lipophilic. 95:" are not synonymous, as can be seen with 239:. Jones & Bartlett Learning. p.  207: 7: 265:Free Radical Biology & Medicine 215:Compendium of Chemical Terminology 25: 48:"friendly") is the ability of a 235:Invitation to Organic Chemistry 279:British Journal of Dermatology 1: 231:Alyn William Johnson (1999). 597:Inorganic nonaqueous solvent 76:. Such compounds are called 684: 582:Acid dissociation constant 26: 547:Solubility table (data) 414:Apparent molar property 221:, accessed 15 Jan 2007. 177:Ionic partition diagram 157:are not amphiphilic or 118:are compounds that are 89:London dispersion force 512:Total dissolved solids 507:Solubility equilibrium 432:and related quantities 612:Partition coefficient 592:Polar aprotic solvent 527:Enthalpy of solution 454:Volume concentration 449:Number concentration 668:Chemical properties 439:Molar concentration 409:Dilution (equation) 187:Lipophilic bacteria 479:Isotopic abundance 444:Mass concentration 318:Chemical solutions 66:non-polar solvents 655: 654: 250:978-0-7637-0432-2 155:fluorosurfactants 50:chemical compound 16:(Redirected from 675: 552:Solubility chart 379:Phase separation 339:Aqueous solution 311: 304: 297: 288: 282: 274: 268: 267:41(8): 1205–1212 261: 255: 254: 238: 228: 222: 212: 44:λίπος "fat" and 21: 683: 682: 678: 677: 676: 674: 673: 672: 658: 657: 656: 651: 561: 522:Solvation shell 493: 431: 423: 419:Miscibility gap 404:Serial dilution 399:Supersaturation 349:Buffer solution 320: 315: 285: 275: 271: 262: 258: 251: 230: 229: 225: 213: 209: 205: 173: 124:surface tension 109: 52:to dissolve in 35: 32: 23: 22: 15: 12: 11: 5: 681: 679: 671: 670: 660: 659: 653: 652: 650: 649: 644: 639: 634: 629: 624: 619: 614: 609: 604: 599: 594: 589: 587:Protic solvent 584: 579: 571: 569: 563: 562: 560: 559: 554: 549: 544: 539: 534: 532:Lattice energy 529: 524: 519: 514: 509: 503: 501: 495: 494: 492: 491: 486: 481: 476: 471: 466: 461: 456: 451: 446: 441: 435: 433: 425: 424: 422: 421: 416: 411: 406: 401: 396: 391: 386: 384:Eutectic point 381: 376: 371: 366: 361: 356: 351: 346: 344:Solid solution 341: 336: 334:Ideal solution 330: 328: 322: 321: 316: 314: 313: 306: 299: 291: 284: 283: 281:, 154:337–340. 269: 256: 249: 223: 206: 204: 201: 200: 199: 194: 189: 184: 179: 172: 169: 108: 105: 33: 24: 14: 13: 10: 9: 6: 4: 3: 2: 680: 669: 666: 665: 663: 648: 645: 643: 640: 638: 635: 633: 630: 628: 625: 623: 620: 618: 615: 613: 610: 608: 605: 603: 600: 598: 595: 593: 590: 588: 585: 583: 580: 577: 573: 572: 570: 568: 564: 558: 555: 553: 550: 548: 545: 543: 540: 538: 535: 533: 530: 528: 525: 523: 520: 518: 515: 513: 510: 508: 505: 504: 502: 500: 496: 490: 487: 485: 482: 480: 477: 475: 474:Mass fraction 472: 470: 469:Mole fraction 467: 465: 462: 460: 457: 455: 452: 450: 447: 445: 442: 440: 437: 436: 434: 430: 429:Concentration 426: 420: 417: 415: 412: 410: 407: 405: 402: 400: 397: 395: 392: 390: 387: 385: 382: 380: 377: 375: 374:Phase diagram 372: 370: 367: 365: 362: 360: 357: 355: 354:Flory–Huggins 352: 350: 347: 345: 342: 340: 337: 335: 332: 331: 329: 327: 323: 319: 312: 307: 305: 300: 298: 293: 292: 289: 280: 273: 270: 266: 260: 257: 252: 246: 242: 237: 236: 227: 224: 220: 216: 211: 208: 202: 198: 197:Microemulsion 195: 193: 192:Lipophobicity 190: 188: 185: 183: 180: 178: 175: 174: 170: 168: 166: 162: 160: 156: 153:By contrast, 151: 149: 145: 144:phospholipids 140: 137: 133: 129: 125: 121: 117: 113: 106: 104: 102: 101:fluorocarbons 98: 94: 90: 85: 83: 79: 75: 71: 67: 63: 59: 55: 51: 47: 43: 39: 38:Lipophilicity 30: 29:Fat fetishism 19: 631: 537:Raoult's law 489:Ternary plot 484:Mixing ratio 278: 272: 264: 259: 234: 226: 210: 163: 152: 141: 110: 86: 77: 37: 36: 642:Lyonium ion 557:Miscibility 542:Henry's law 120:amphiphilic 116:surfactants 112:Hydrocarbon 107:Surfactants 93:hydrophobic 82:hydrophilic 18:Fat-soluble 637:Amphiphile 632:Lipophilic 627:Hydrophile 622:Hydrophobe 499:Solubility 394:Saturation 364:Suspension 219:lipophilic 203:References 165:Oxybenzone 159:detergents 78:lipophilic 647:Lyate ion 602:Solvation 517:Solvation 459:Normality 148:phosphate 128:emulsions 97:silicones 662:Category 617:Polarity 576:Category 464:Molality 326:Solution 171:See also 136:Micelles 132:micelles 68:such as 567:Solvent 369:Colloid 359:Mixture 114:-based 74:toluene 247:  70:hexane 64:, and 62:lipids 40:(from 389:Alloy 182:ITIES 46:φίλος 42:Greek 245:ISBN 99:and 58:oils 54:fats 241:283 72:or 664:: 243:. 217:, 60:, 56:, 578:) 574:( 310:e 303:t 296:v 253:. 31:. 20:)

Index

Fat-soluble
Fat fetishism
Greek
φίλος
chemical compound
fats
oils
lipids
non-polar solvents
hexane
toluene
hydrophilic
London dispersion force
hydrophobic
silicones
fluorocarbons
Hydrocarbon
surfactants
amphiphilic
surface tension
emulsions
micelles
Micelles
phospholipids
phosphate
fluorosurfactants
detergents
Oxybenzone
Ionic partition diagram
ITIES

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