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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 20:22:28 UTC
NP-MRD IDNP0000014
Secondary Accession NumbersNone
Natural Product Identification
Common NameTrehalose
DescriptionTrehalose, also known as mycose, is a 1-alpha (disaccharide) sugar found extensively but not abundantly in nature. It is thought to be implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation. The sugar is thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, generally lethal damage that would normally follow a dehydration/reyhdration cycle. Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of alpha-D-glucopyranoglucopyranosyl-1,1-alpha-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). The enzyme trehalase, present but not abundant in most people, breaks it into two glucose molecules, which can then be readily absorbed in the gut. Trehalose is an important components of insects circulating fluid. It acts as a storage form of insect circulating fluid and it is important in respiration. Trehalose has also been found to be a metabolite of Burkholderia, Escherichia and Propionibacterium (PMID: 12105274 ; PMID: 25479689 ) (Krishikosh.Egranth.Ac.In/bitstream/1/84382/1/88571%20P-1257.Pdf).
Structure
Thumb
Synonyms
ValueSource
(GLC)2ChEBI
alpha,Alpha'-trehaloseChEBI
alpha-D-GLCP-(11)-alpha-D-GLCPChEBI
alpha-D-Glucopyranosyl-alpha-D-glucopyranosideChEBI
alpha-D-TrehaloseChEBI
alpha-TrehaloseChEBI
D-(+)-TrehaloseChEBI
Ergot sugarChEBI
MycoseChEBI
a,Alpha'-trehaloseGenerator
Α,alpha'-trehaloseGenerator
a-D-GLCP-(11)-a-D-GLCPGenerator
Α-D-GLCP-(11)-α-D-GLCPGenerator
a-D-Glucopyranosyl-a-D-glucopyranosideGenerator
Α-D-glucopyranosyl-α-D-glucopyranosideGenerator
a-D-TrehaloseGenerator
Α-D-trehaloseGenerator
a-TrehaloseGenerator
Α-trehaloseGenerator
alpha,alpha-TrehaloseHMDB
D-Trehalose-anhydrousHMDB
delta-Trehalose-anhydrousHMDB
D-TrehaloseHMDB
Natural trehaloseHMDB
O-D-Glucopyranosyl-(1→1)-D-glucopyranosideHMDB
alpha,Alpha'-D-trehaloseHMDB
alpha-D-Glucopyranosyl alpha-D-glucopyranosideHMDB
Α,α'-D-trehaloseHMDB
Α,α-trehaloseHMDB
Α,α’-D-trehaloseHMDB
Α-D-glucopyranosyl α-D-glucopyranosideHMDB
TrehaloseHMDB
Chemical FormulaC12H22O11
Average Mass342.2965 Da
Monoisotopic Mass342.11621 Da
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol
Traditional Nameα,α'-trehalose
CAS Registry Number99-20-7
SMILES
OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
InChI KeyHDTRYLNUVZCQOY-LIZSDCNHSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
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)Varshavi.d262021-07-19View 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 thalianaKNApSAcK Database
Arachis hypogaea
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
Bacteria
      Not Available
Basella alba
Benincasa hispida
Bertholletia excelsa
Beta vulgaris
Beta vulgaris ssp. cicla
Bison bison
Borago officinalis
Bos taurus
Bos taurus X Bison bison
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napus
Brassica oleracea
Brassica oleracea L. ssp. BotrytisKNApSAcK Database
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 carvi
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 X sinensis (L.) Osbeck (pro. sp.)
Cocos nucifera
Coffea arabica L.
Coffea canephora
Colocasia esculenta
Columba
Columbidae
Corchorus olitorius
Coriandrum sativum L.
Corylus
Corylus avellana
Crateva religiosa
Crocus sativus
Cucumis melo
Cucumis metuliferus
Cucumis sativus L.
Cucurbita
Cucurbita maxima
Cucurbita moschata
Cuminum cyminum
Curcuma domesticaKNApSAcK Database
Curcuma longaPlant
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
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 japonica
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
Fungi
      Not Available
Gallus gallus
Garcinia mangostana
Gaylussacia baccata
Ginkgo biloba
Glycine max
Gossypium
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.
Helianthus tuberosus
Hibiscus sabbariffa
Hippophae rhamnoides
Hordeum vulgare
Hyssopus officinalis L.
Illicium verum
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
Lepidium sativum
Leporidae
Lepus timidus
Levisticum officinale
Linum usitatissimum
Litchi chinensis
Luffa aegyptiaca
Lupinus
Lupinus albus
Macadamia
Macadamia tetraphylla
Malpighia emarginata
Malus
Malus pumila
Mammea americana
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativa
Melanitta fusca
Meleagris gallopavo
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicata
Mentha x piperita
Mespilus germanica
Metazoa
      Not Available
Metroxylon sagu
Momordica charantia
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
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 ginseng
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
Phoenix dactylifera
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
Pleurotus ostreatus
Polygonum alpinum
Portulaca oleracea
Pouteria sapota
Prunus armeniaca
Prunus aviumKNApSAcK Database
Prunus avium L.
Prunus cerasus
Prunus domestica
Prunus dulcis
Prunus persica
Prunus persica var. nucipersica
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Psidium cattleianum
Psidium guajava
Psophocarpus tetragonolobus
Punica granatum
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 idaeus
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
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
Selaginella involvens-
Selaginella lepidophylla-
Selaginella tamariscina-
Sesamum indicum
Sesbania bispinosa
Sinapis alba
Sisymbrium
Solanum lycopersicumPlant
Solanum lycopersicum L.KNApSAcK Database
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicum
Solanum melongena
Solanum quitoense
Solanum tuberosum
Sorbus aucuparia
Sorghum bicolorPlant
Sorghum vulgareKNApSAcK Database
Spinacia oleracea
Sporobolus stapfianusKNApSAcK Database
Struthio camelus
Sus scrofa
Sus scrofa domestica
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indica
Taraxacum officinale
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
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
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
Agaricus campestrisKNApSAcK Database
Amanita muscariaKNApSAcK Database
Bombyx moriKNApSAcK Database
Lentinus edodesKNApSAcK Database
Phellinus igniariusKNApSAcK Database
Streptomyces coelicolor A3(2)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203 °Chttps://en.wikipedia.org/wiki/Trehalose
Boiling Point586.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.69 mg/mL at 20 °CNot Available
LogP-1.650 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility592 g/LALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS0.24ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000975
DrugBank IDDB12310
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031220
KNApSAcK IDC00001152
Chemspider ID7149
KEGG Compound IDC01083
BioCyc IDTREHALOSE
BiGG ID36774
Wikipedia LinkTrehalose
METLIN ID5913
PubChem Compound7427
PDB IDNot Available
ChEBI ID16551
Good Scents IDrw1701121
References
General References
  1. Potier M, Dallaire L, Melancon SB: Occurrence and properties of fetal intestinal glycosidases (disaccharidases) in human amniotic fluid. Biol Neonate. 1975;27(3-4):141-52. [PubMed:241430 ]
  2. Citron DM, Baron EJ, Finegold SM, Goldstein EJ: Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species. J Clin Microbiol. 1990 Oct;28(10):2220-3. [PubMed:2229345 ]
  3. Yoshioka S, Aso Y: A quantitative assessment of the significance of molecular mobility as a determinant for the stability of lyophilized insulin formulations. Pharm Res. 2005 Aug;22(8):1358-64. Epub 2005 Aug 3. [PubMed:16078146 ]
  4. Guo N, Puhlev I, Brown DR, Mansbridge J, Levine F: Trehalose expression confers desiccation tolerance on human cells. Nat Biotechnol. 2000 Feb;18(2):168-71. [PubMed:10657122 ]
  5. Nie Y, de Pablo JJ, Palecek SP: Platelet cryopreservation using a trehalose and phosphate formulation. Biotechnol Bioeng. 2005 Oct 5;92(1):79-90. [PubMed:15937943 ]
  6. Fujita Y, Naka T, Doi T, Yano I: Direct molecular mass determination of trehalose monomycolate from 11 species of mycobacteria by MALDI-TOF mass spectrometry. Microbiology. 2005 May;151(Pt 5):1443-52. [PubMed:15870454 ]
  7. Lu FQ, Liu JH, Ouyang XL, Li XJ, Zhou J, Zhuang Y: [Process of human platelets loaded with rehalose before lyophilization]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2006 Feb;14(1):156-61. [PubMed:16584614 ]
  8. Shirkhanzadeh M: Microneedles coated with porous calcium phosphate ceramics: effective vehicles for transdermal delivery of solid trehalose. J Mater Sci Mater Med. 2005 Jan;16(1):37-45. [PubMed:15754142 ]
  9. Eroglu A, Russo MJ, Bieganski R, Fowler A, Cheley S, Bayley H, Toner M: Intracellular trehalose improves the survival of cryopreserved mammalian cells. Nat Biotechnol. 2000 Feb;18(2):163-7. [PubMed:10657121 ]
  10. Arguelles JC, Rodriguez T, Alvarez-Peral FJ: Trehalose hydrolysis is not required for human serum-induced dimorphic transition in Candida albicans: evidence from a tps1/tps1 mutant deficient in trehalose synthesis. Res Microbiol. 1999 Oct;150(8):521-9. [PubMed:10577485 ]
  11. Corning BF, Murphy JC, Fox JG: Group G streptococcal lymphadenitis in rats. J Clin Microbiol. 1991 Dec;29(12):2720-3. [PubMed:1757539 ]
  12. Davies JE, Sarkar S, Rubinsztein DC: Trehalose reduces aggregate formation and delays pathology in a transgenic mouse model of oculopharyngeal muscular dystrophy. Hum Mol Genet. 2006 Jan 1;15(1):23-31. Epub 2005 Nov 25. [PubMed:16311254 ]
  13. Ma X, Jamil K, Macrae TH, Clegg JS, Russell JM, Villeneuve TS, Euloth M, Sun Y, Crowe JH, Tablin F, Oliver AE: A small stress protein acts synergistically with trehalose to confer desiccation tolerance on mammalian cells. Cryobiology. 2005 Aug;51(1):15-28. [PubMed:15963489 ]
  14. Alcoba-Florez J, Mendez-Alvarez S, Cano J, Guarro J, Perez-Roth E, del Pilar Arevalo M: Phenotypic and molecular characterization of Candida nivariensis sp. nov., a possible new opportunistic fungus. J Clin Microbiol. 2005 Aug;43(8):4107-11. [PubMed:16081957 ]
  15. Chang L, Shepherd D, Sun J, Ouellette D, Grant KL, Tang XC, Pikal MJ: Mechanism of protein stabilization by sugars during freeze-drying and storage: native structure preservation, specific interaction, and/or immobilization in a glassy matrix? J Pharm Sci. 2005 Jul;94(7):1427-44. [PubMed:15920775 ]
  16. Sasnoor LM, Kale VP, Limaye LS: A combination of catalase and trehalose as additives to conventional freezing medium results in improved cryoprotection of human hematopoietic cells with reference to in vitro migration and adhesion properties. Transfusion. 2005 Apr;45(4):622-33. [PubMed:15819685 ]
  17. Alvarez-Peral FJ, Arguelles JC: Changes in external trehalase activity during human serum-induced dimorphic transition in Candida albicans. Res Microbiol. 2000 Dec;151(10):837-43. [PubMed:11191809 ]
  18. Berlutti F, Thaller MC, Dainelli B, Pezzi R: T-mod pathway, a reduced sequence for identification of gram-negative urinary tract pathogens. J Clin Microbiol. 1989 Jul;27(7):1646-9. [PubMed:2768451 ]
  19. Kandror O, DeLeon A, Goldberg AL: Trehalose synthesis is induced upon exposure of Escherichia coli to cold and is essential for viability at low temperatures. Proc Natl Acad Sci U S A. 2002 Jul 23;99(15):9727-32. doi: 10.1073/pnas.142314099. Epub 2002 Jul 8. [PubMed:12105274 ]
  20. Habe H, Sato S, Morita T, Fukuoka T, Kirimura K, Kitamoto D: Bacterial production of short-chain organic acids and trehalose from levulinic acid: a potential cellulose-derived building block as a feedstock for microbial production. Bioresour Technol. 2015 Feb;177:381-6. doi: 10.1016/j.biortech.2014.11.048. Epub 2014 Nov 18. [PubMed:25479689 ]