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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:11 UTC
NP-MRD IDNP0001099
Secondary Accession NumbersNone
Natural Product Identification
Common NameSorbitol
DescriptionSorbitol is a polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally and is also produced synthetically from glucose. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. It is also used in many manufacturing processes, as a pharmaceutical aid, and in several research applications. Ascorbic acid fermentation; in solution form for moisture-conditioning of cosmetic creams and lotions, toothpaste, tobacco, gelatin; bodying agent for paper, textiles, and liquid pharmaceuticals; softener for candy; sugar crystallization inhibitor; surfactants; urethane resins and rigid foams; plasticizer, stabilizer for vinyl resins; food additive (sweetener, humectant, emulsifier, thickener, anticaking agent); dietary supplement. (Hawley's Condensed Chemical Dictionary) Biological Source: Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus species Use/Importance: Used for manufacturing of sorbose, propylene glycol, ascorbic acid, resins, plasticizers and as antifreeze mixtures with glycerol or glycol. Tablet diluent, sweetening agent and humectant, other food uses. Sorbitol is used in photometric determination of Ru(VI) and Ru(VIII); in acid-base titration of borate (Dictionary of Organic Compounds).
Structure
Thumb
Synonyms
ValueSource
(-)-SorbitolChEBI
(2R,3R,4R,5S)-Hexane-1,2,3,4,5,6-hexolChEBI
D-(-)-SorbitolChEBI
D-SorbitChEBI
D-SORBITOLChEBI
e 420ChEBI
e-420ChEBI
e420ChEBI
g-OlChEBI
GLC-OlChEBI
L-GulitolChEBI
D-GlucitolKegg
Sorbitol 3% in plastic containerKegg
D-SorbolHMDB
DiakarmonHMDB
EsasorbHMDB
Foodol D 70HMDB
GlucarineHMDB
GlucitolHMDB
KarionHMDB
Karion instantHMDB
Kyowa powder 50mHMDB
MultitolHMDB
NeosorbHMDB
Neosorb 20/60dCHMDB
Neosorb 70/02HMDB
Neosorb 70/70HMDB
Neosorb p 20/60HMDB
Neosorb p 60HMDB
Neosorb p 60WHMDB
NivitinHMDB
ResulaxHMDB
SionitHMDB
Sionit KHMDB
SioniteHMDB
SiononHMDB
SiosanHMDB
Sorbex mHMDB
Sorbex RHMDB
Sorbex RPHMDB
Sorbex SHMDB
Sorbex XHMDB
SorbilandeHMDB
SorbilaxHMDB
SorbitHMDB
Sorbit D 70HMDB
Sorbit D-powderHMDB
Sorbit DPHMDB
Sorbit DP 50HMDB
Sorbit kyowa powder 50mHMDB
Sorbit L 70HMDB
Sorbit SHMDB
Sorbit T 70HMDB
Sorbit W 70HMDB
Sorbit W-powderHMDB
Sorbit W-powder 50HMDB
Sorbit WPHMDB
SorbiteHMDB
Sorbitol FHMDB
Sorbitol FKHMDB
Sorbitol FPHMDB
Sorbitol SHMDB
Sorbitol syrup CHMDB
SorbiturHMDB
SorboHMDB
Sorbogem 712HMDB
SorbolHMDB
SorbostylHMDB
Medefield brand OF sorbitolHMDB
Sorbitol pfizer brandHMDB
YalHMDB
Klysma sorbitHMDB
MedevacHMDB
Trommsdorff brand OF sorbitolHMDB
Baxter brand OF sorbitolHMDB
Pfizer brand OF sorbitolHMDB
Chemical FormulaC6H14O6
Average Mass182.1718 Da
Monoisotopic Mass182.07904 Da
IUPAC Name(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional NameD-sorbitol
CAS Registry Number50-70-4
SMILES
OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
InChI KeyFBPFZTCFMRRESA-JGWLITMVSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-12View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentus
Actinidia chinensis
Agaricus bisporus
Agave
Allium ampeloprasum
Allium ascalonicum
Allium cepa
Allium cepa L.
Allium fistulosum
Allium sativum
Allium schoenoprasum
Allium tuberosum
Aloysia triphylla
Amaranthus
Amelanchier alnifolia
Anacardium occidentale
Ananas comosus
Anas platyrhynchos
Anatidae
Anethum graveolens
Angelica keiskei
Annona cherimola
Annona muricata
Annona reticulata
Annona squamosa
Anser anser
Anthriscus cerefolium
Apium graveolens
Apium graveolens var. dulce
Apium graveolens var. rapaceum
Apium graveolens var. secalinum
Arabidopsis thaliana
Arachis hypogaea
Aragoa cundinamarcensisKNApSAcK Database
Arctium lappa
Armoracia rusticana
Artemisia dracunculus
Artemisia vulgaris
Artocarpus altilis
Artocarpus heterophyllus
Asparagus officinalis
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.
Averrhoa carambolaKNApSAcK Database
Basella alba
Benincasa hispida
Bertholletia excelsa
Beta vulgaris
Beta vulgaris ssp. cicla
Bifurcaria bifurcata
Bison bison
Borago officinalis
Bos taurus
Bos taurus X Bison bison
Bostrychia tenella
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napus
Brassica oleracea
Brassica oleracea var. botrytis
Brassica oleracea var. capitata
Brassica oleracea var. gemmifera
Brassica oleracea var. gongylodes
Brassica oleracea var. italica
Brassica oleracea var. sabauda
Brassica oleracea var. viridis
Brassica rapa
Brassica rapa ssp. chinensis
Brassica rapa var. pekinensis
Brassica rapa var. rapa
Brassica ruvo
Brosimum alicastrum
Bubalus bubalis
Byrsonima crassifolia
Cajanus cajan
Canarium ovatum
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibarius
Capparis spinosa
Capra aegagrus hircus
Capsicum annuum
Capsicum annuum L.
Capsicum annuum var. annuum
Capsicum chinense
Capsicum pubescens
Carica papaya L.
Carissa macrocarpa
Carthamus tinctorius
Carum carviFooDB
Carum carvi L.KNApSAcK Database
Carya
Carya illinoinensis
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Ceratonia siliqua
Cervidae
Cervus canadensis
Chamaemelum nobile
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chrysanthemum coronarium
Cicer arietinum
Cichorium endivia
Cichorium intybus
Cinnamomum
Cinnamomum aromaticum
Cinnamomum verum
Cirsium
Citrullus lanatus
Citrus ×limon (L.) Burm. f. (pro sp.)
Citrus aurantiifolia
Citrus latifolia
Citrus limon
Citrus maxima
Citrus paradisi
Citrus reticulata
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)
Cocos nuciferaKNApSAcK Database
Coffea arabica L.
Coffea canephora
Colocasia esculenta
Columba
Columbidae
Corchorus olitorius
Coriandrum sativum L.
Corylus
Corylus avellana
Crataegus spp.KNApSAcK Database
Crateva religiosa
Crocus sativus
Cucumis melo
Cucumis metuliferus
Cucumis sativus L.
Cucurbita
Cucurbita maxima
Cucurbita moschata
Cuminum cyminum
Curcuma longa
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
Dalea scandens
Daucus carota
Daucus carota ssp. sativus
Dimocarpus longan
Dioscorea
Dioscorea pentaphylla
Diospyros
Diospyros kaki
Diospyros virginiana
Dromaius novaehollandiae
Durio zibethinus
Dysphania ambrosioides
Elaeis
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
Equus caballus
Eragrostis tef
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. Sativa
Eugenia javanica
Eugenia uniflora
Eutrema japonicum
Fagopyrum esculentum
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus carica
Flammulina velutipes
Foeniculum vulgare
Fragaria x ananassa
Gallus gallus
Garcinia mangostana
Gaylussacia baccata
Ginkgo biloba
Glycine max
Gossypium
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.
Helianthus tuberosus
Heptapleurum bodinieri
Hibiscus sabbariffa
Hippophae rhamnoides
Homo sapiens
Hordeum vulgare
Hyssopus officinalis L.
Illicium verum
Inonotus obliquus
Ipomoea aquatica
Ipomoea batatas
Juglans
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.
Juglans regia
Lablab purpureus
Lactuca sativa
Lagenaria siceraria
Lagopus muta
Lathyrus sativus
Laurus nobilis L.
Lens culinaris
Lentinus edodes
Lepidium sativum
Leporidae
Lepus timidus
Levisticum officinale
Ligustrum robustum
Linum usitatissimum
Litchi chinensis
Litoria verreauxii
Lotus corniculatus
Luffa aegyptiaca
Lupinus
Lupinus albus
Macadamia
Macadamia tetraphylla
Malpighia emarginata
Malus
Malus pumilaFooDB
Mammea americana
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativaKNApSAcK Database
Melanitta fusca
Meleagris gallopavo
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicata
Mentha x piperita
Mespilus germanica
Metroxylon sagu
Momordica charantia
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
Mus musculus
Musa acuminata
Musa x paradisiaca
Myrica
Myristica fragrans
Nelumbo
Nelumbo nucifera
Nephelium lappaceum
Numida meleagris
Nuphar lutea
Ocimum basilicum
Odocoileus
Oenothera biennis
Olea europaea
Opuntia
Opuntia cochenillifera
Opuntia macrorhiza
Origanum majorana
Origanum onites
Origanum vulgare
Origanum X majoricum
Oryctolagus
Oryza rufipogon
Oryza sativa
Ovis aries
Pachyrhizus erosus
Panax ginsengKNApSAcK Database
Pangium edule
Panicum miliaceum
Passiflora edulis
Pastinaca sativa
Pediomelum esculentum
Perideridia oregana
Persea americana
Petasites japonicus
Petroselinum crispum
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgaris
Phasianidae
Phasianus colchicus
Phellinus igniarius
Phoenix dactyliferaFooDB
Photinia melanocarpa
Phyllostachys edulis
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioica
Pimpinella anisum
Pinus
Pinus edulis
Piper nigrum L.
Pistacia vera
Pisum sativum
Plantago creticaKNApSAcK Database
Plantago subspathulataKNApSAcK Database
Pleurotus ostreatus
Pogostemon cablin
Polygonum alpinum
Portulaca oleracea
Pouteria sapota
Prunus armeniacaFooDB
Prunus aviumKNApSAcK Database
Prunus avium L.
Prunus cerasusFooDB
Prunus domestica
Prunus dulcis
Prunus laurocerasus
Prunus padus
Prunus persica
Prunus persica var. nucipersica
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Psidium cattleianum
Psidium guajava
Psophocarpus tetragonolobus
Punica granatumFooDB
Pyrus communis
Pyrus pyrifolia
Quercus
Raphanus sativus
Raphanus sativus var. longipinnatus
Raphanus sativus var. sativus
Rheum rhabarbarum
Ribes aureum
Ribes glandulosum
Ribes nigrum
Ribes rubrum
Ribes uva-crispa
Rosa
Rubus arcticus
Rubus chamaemorus
Rubus idaeusFooDB
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
Salacia chinensis
Salix pulchra
Salvia elegans
Salvia hispanica
Salvia officinalis
Salvia rosmarinus
Sambucus nigra
Sambucus nigra L.
Satureja hortensis L.
Satureja montana
Scorzonera hispanica
Secale cereale
Sechium edule
Sesamum indicum
Sesbania bispinosa
Sinapis alba
Sisymbrium
Solanum lycopersicum
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicum
Solanum melongena
Solanum quitoense
Solanum tuberosum
Sorbus aucupariaKNApSAcK Database
Sorghum bicolor
Spinacia oleracea
Struthio camelus
Sus scrofa
Sus scrofa domestica
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indica
Taraxacum officinale
Tetrachondra hamiltonii
Tetragonia tetragonioides
Thelesperma
Thymus pulegioides
Thymus vulgaris
Tilia cordata
Tilia L.
Tragopogon porrifolius
Trigonella foenum-graecum
Triticum
Triticum aestivum
Triticum durum
Triticum spelta
Triticum turanicum
Trypanosoma brucei
Typha angustifolia
Vaccinium
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarpon
Vaccinium myrtilloides
Vaccinium myrtillus
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaea
Valerianella locusta
Vanilla
Verbena officinalis
Viburnum edule
Vicia faba
Vigna aconitifolia
Vigna angularis
Vigna mungo
Vigna radiata
Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculata
Vigna unguiculata var. sesquipedalis
Viscum album
Vitis
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.
Xanthosoma sagittifolium
Zea mays L.
Zingiber officinale
Zizania
Zizania aquatica
Ziziphus zizyphus
Species Where Detected
Species NameSourceReference
Escherichia coli K12KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point11 °CNot Available
Boiling Point494.00 to 495.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2750 mg/mLNot Available
LogP-2.20Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility229 g/LALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m³·mol⁻¹ChemAxon
Polarizability17.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000247
DrugBank IDDB01638
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030799
KNApSAcK IDC00001173
Chemspider ID5576
KEGG Compound IDC00794
BioCyc IDSORBITOL
BiGG IDNot Available
Wikipedia LinkSorbitol
METLIN IDNot Available
PubChem Compound5780
PDB IDNot Available
ChEBI ID17924
Good Scents IDrw1034721
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Airey CM, Price DE, Kemp JV, Perkins CM, Wales JK: The effect of aldose reductase inhibition on erythrocyte polyols and galactitol accumulation in diabetic patients. Diabet Med. 1989 Dec;6(9):804-8. [PubMed:2533041 ]
  3. Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. [PubMed:7710082 ]
  4. Sundkvist G, Dahlin LB, Nilsson H, Eriksson KF, Lindgarde F, Rosen I, Lattimer SA, Sima AA, Sullivan K, Greene DA: Sorbitol and myo-inositol levels and morphology of sural nerve in relation to peripheral nerve function and clinical neuropathy in men with diabetic, impaired, and normal glucose tolerance. Diabet Med. 2000 Apr;17(4):259-68. [PubMed:10821291 ]
  5. Morenkova SA: [Comparative analysis of dependence of saliva sorbitol and fructosamine levels on blood glucose level in patients with diabetes]. Biomed Khim. 2004;50(6):612-4. [PubMed:15707277 ]
  6. Bareford D, Jennings PE, Stone PC, Baar S, Barnett AH, Stuart J: Effects of hyperglycaemia and sorbitol accumulation on erythrocyte deformability in diabetes mellitus. J Clin Pathol. 1986 Jul;39(7):722-7. [PubMed:3090107 ]
  7. Ciuchi E, Odetti P, Prando R: Relationship between glutathione and sorbitol concentrations in erythrocytes from diabetic patients. Metabolism. 1996 May;45(5):611-3. [PubMed:8622605 ]
  8. Kwang-Hyok S, Ui-Nam P, Sarkar C, Bhadra R: A sensitive assay of red blood cell sorbitol level by high performance liquid chromatography: potential for diagnostic evaluation of diabetes. Clin Chim Acta. 2005 Apr;354(1-2):41-7. Epub 2005 Jan 18. [PubMed:15748598 ]
  9. Nau R: Osmotherapy for elevated intracranial pressure: a critical reappraisal. Clin Pharmacokinet. 2000 Jan;38(1):23-40. [PubMed:10668857 ]
  10. Belanger DR, Tierney MG, Dickinson G: Effect of sodium polystyrene sulfonate on lithium bioavailability. Ann Emerg Med. 1992 Nov;21(11):1312-5. [PubMed:1416324 ]
  11. Ciuchi E, Odetti P, Prando R: The effect of acute glutathione treatment on sorbitol level in erythrocytes from diabetic patients. Diabetes Metab. 1997 Feb;23(1):58-60. [PubMed:9059767 ]
  12. Shinohara R, Ohta Y, Yamauchi M, Ishiguro I: Improved fluorometric enzymatic sorbitol assay in human blood. Clin Chim Acta. 1998 May 25;273(2):171-84. [PubMed:9657347 ]
  13. Peterson MJ, Page MG, Just LJ, Aldinger CE, Malone JI: Applicability of red blood cell sorbitol measurements to monitor the clinical activity of sorbinil. Metabolism. 1986 Apr;35(4 Suppl 1):93-5. [PubMed:3515121 ]
  14. Vertommen J, Rillaerts E, Gysels M, De Leeuw I: Erythrocyte sorbitol content in diabetic patients: relation to metabolic control. Diabete Metab. 1987 Jun;13(3):182-6. [PubMed:3301442 ]
  15. Cunningham JJ, Mearkle PL, Brown RG: Vitamin C: an aldose reductase inhibitor that normalizes erythrocyte sorbitol in insulin-dependent diabetes mellitus. J Am Coll Nutr. 1994 Aug;13(4):344-50. [PubMed:7963139 ]
  16. Kamon N, Mabuchi H, Takeda R, Terashima H: Effects of aldose reductase inhibitor (ONO-2235) on human erythrocyte sorbitol concentrations in 75 g oral glucose tolerance tests. Horm Metab Res. 1991 May;23(5):226-9. [PubMed:1908433 ]
  17. Sizeland PC, Chambers ST, Lever M, Bason LM, Robson RA: Short-term response of nonurea organic osmolytes in human kidney to a water load and water deprivation. Am J Physiol. 1995 Feb;268(2 Pt 2):F227-33. [PubMed:7864160 ]
  18. van Griensven JM, Jusko WJ, Lemkes HH, Kroon R, Verhorst CJ, Chiang ST, Cohen AF: Tolrestat pharmacokinetic and pharmacodynamic effects on red blood cell sorbitol levels in normal volunteers and in patients with insulin-dependent diabetes. Clin Pharmacol Ther. 1995 Dec;58(6):631-40. [PubMed:8529328 ]
  19. Regenold WT, Kling MA, Hauser P: Elevated sorbitol concentration in the cerebrospinal fluid of patients with mood disorders. Psychoneuroendocrinology. 2000 Aug;25(6):593-606. [PubMed:10840171 ]
  20. Gehring H, Hornberger C, Dibbelt L, Dorges V, Eichenauer R, Schmucker P: Detecting and quantifying absorbed irrigation fluid by measuring mannitol and sorbitol concentrations in serum samples, and by ethanol monitoring. BJU Int. 2002 Feb;89(3):202-7. [PubMed:11856099 ]
  21. Burggraaf J, Schoemaker RC, Lentjes EG, Cohen AF: Sorbitol as a marker for drug-induced decreases of variable duration in liver blood flow in healthy volunteers. Eur J Pharm Sci. 2000 Dec;12(2):133-9. [PubMed:11102741 ]