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Chemistry

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Also known as: 56038-13-2, Trichlorosucrose, Splenda, Aspasvit, Trichlorogalacto-sucrose, 96k6uq3zd4
Molecular Formula
C12H19Cl3O8
Molecular Weight
397.6  g/mol
InChI Key
BAQAVOSOZGMPRM-QBMZZYIRSA-N
FDA UNII
96K6UQ3ZD4

Acucar Light
sweetness intensity roughly 600 times that of sucrose and is nonnutritive and noncaloric; largely unabsorbed in the gastrointestinal tract
1 2D Structure

Acucar Light

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,3R,4R,5R,6R)-2-[(2R,3S,4S,5S)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-5-chloro-6-(hydroxymethyl)oxane-3,4-diol
2.1.2 InChI
InChI=1S/C12H19Cl3O8/c13-1-4-7(17)10(20)12(3-14,22-4)23-11-9(19)8(18)6(15)5(2-16)21-11/h4-11,16-20H,1-3H2/t4-,5-,6+,7-,8+,9-,10+,11-,12+/m1/s1
2.1.3 InChI Key
BAQAVOSOZGMPRM-QBMZZYIRSA-N
2.2 Other Identifiers
2.2.1 UNII
96K6UQ3ZD4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Trichlorosucrose

2. 1',4',6'-trichloro-1',4,6'-trideoxygalactosucrose

3. 1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl-4-chloro-4-deoxy-alpha-d-galactopyranoside

4. Trichlorogalacto-sucrose

5. Trichlorogalactosucrose

6. Splenda

2.3.2 Depositor-Supplied Synonyms

1. 56038-13-2

2. Trichlorosucrose

3. Splenda

4. Aspasvit

5. Trichlorogalacto-sucrose

6. 96k6uq3zd4

7. Sucrazit

8. Trichlorogalactosucrose

9. Chebi:32159

10. Sansweet Su 100

11. Dtxsid1040245

12. 4,1',6'-trichlorogalactosucrose

13. San Sweet Sa 8020

14. 1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl 4-chloro-4-deoxy-alpha-d-galactopyranoside

15. 1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl-4-chloro-4-deoxy-alpha-d-galactopyranoside

16. Nsc-759272

17. Ins No.955

18. Dtxcid9020245

19. Ins-955

20. Alpha-d-galactopyranoside, 1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl 4-chloro-4-deoxy-

21. 1',4',6'-trichloro-galactosucrose

22. E-955

23. (2r,3r,4r,5r,6r)-2-[(2r,3s,4s,5s)-2,5-bis(chloromethyl)-3,4-dihydroxy-tetrahydrofuran-2-yl]oxy-5-chloro-6-(hydroxymethyl)tetrahydropyran-3,4-diol

24. (2r,3r,4r,5r,6r)-2-((2r,3s,4s,5s)-2,5-bis(chloromethyl)-3,4-dihydroxy-tetrahydrofuran-2-yl)oxy-5-chloro-6-(hydroxymethyl)tetrahydropyran-3,4-diol

25. Refchem:6267

26. Glytoucan:g30984wq

27. 1',4',6'-trichloro-1',4,6'-trideoxygalactosucrose

28. G30984wq

29. 259-952-2

30. 1',4,6'-trichlorogalactosucrose

31. Einecs 259-952-2

32. Mfcd03648615

33. C12h19cl3o8

34. Chembl3185084

35. A-d-galactopyranoside, 1,6-dichloro-1,6-dideoxy-b-d-fructofuranosyl4-chloro-4-deoxy-

36. (2r,3r,4r,5r,6r)-2-(((2r,3s,4s,5s)-2,5-bis(chloromethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)-5-chloro-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4-diol

37. Acucar Light

38. (2r,3r,4r,5r,6r)-2-[(2r,3s,4s,5s)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-5-chloro-6-(hydroxymethyl)oxane-3,4-diol

39. .alpha.-d-galactopyranoside, 1,6-dichloro-1,6-dideoxy-.beta.-d-fructofuranosyl 4-chloro-4-deoxy-

40. 4,1',6'-trichloro-4,1',6'-trideoxy-galacto-sucrose

41. E955;trichlorosucrose

42. Unii-96k6uq3zd4

43. Cas-56038-13-2

44. Brn 3654410

45. Sucralose [ban:nf]

46. Ccris 8449

47. Hsdb 7964

48. Sucralose; 1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl 4-chloro-4-deoxy-alpha-d-galactopyranoside

49. E955

50. Sucralose [fcc]

51. Sucralose [ii]

52. Sucralose [mi]

53. Sucralose [mart.]

54. Schembl3686

55. Sucralose [usp-rs]

56. Sucralose [who-dd]

57. 1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl 4-chloro-4-deoxy-alpha-d-galactose

58. Sucralose, Analytical Standard

59. Orb1308737

60. Sucralose [ep Monograph]

61. Msk3215

62. Baqavosozgmprm-qbmzzyirsa-n

63. Hms2093h16

64. Pharmakon1600-01505953

65. Hy-n0614

66. Sucralose, >=98.0% (hplc)

67. Tox21_113658

68. Tox21_201752

69. Tox21_303425

70. Bdbm50367128

71. Nsc759272

72. S4214

73. Akos015962432

74. Ccg-213995

75. Cs-8130

76. Nsc 759272

77. Os04165

78. Ncgc00249110-01

79. Ncgc00249110-03

80. Ncgc00249110-04

81. Ncgc00257400-01

82. Ncgc00259301-01

83. 1-(1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl)-4-chloro-4-deoxy-alpha-d-galactopyranoside

84. Sbi-0206860.p001

85. Sucralose 1000 Microg/ml In Acetonitrile

86. Ns00000320

87. Ab01563242_01

88. Ab01563242_02

89. 038s132

90. Q410209

91. Sr-05000001935

92. Sr-05000001935-1

93. Brd-k58968598-001-02-8

94. Brd-k58968598-001-03-6

95. Sucralose, European Pharmacopoeia (ep) Reference Standard

96. Sucralose, United States Pharmacopeia (usp) Reference Standard

97. Sucralose, Pharmaceutical Secondary Standard; Certified Reference Material

98. 1,6-dichloro-1,6-dideoxy-b-d-fructofuranosyl-4-chloro-4-deoxy-a-d-galactopyranoside

99. 1,6-dichloro-1,6-dideoxy-.beta.-d-fructofuranosyl-4-chloro-4-deoxy-.alpha.-d-galactopyranoside

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 397.6 g/mol
Molecular Formula C12H19Cl3O8
XLogP3-1.5
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area129
Heavy Atom Count23
Formal Charge0
Complexity405
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Sweetening Agents

Substances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed)


4.2 Absorption, Distribution and Excretion

After single intravenous doses of (14)C-trichlorogalactosucrose to dogs at a dose level of 2 mg/kg (5.8 uCi/kg) radioactivity was rapidly excreted mainly in the urine. Urinary excretion accounted for means of 29.3%, 63.9% and 74.1% of the dose during 3, 6 and 12 hours after dosing respectively, increasing to 80.9% of the dose after 5 days. Fecal excretion accounted for a mean of 10.4% dose after 24 hours, increasing to 11.9% dose after 5 days. Plasma radioactivity was maximal at 5 minutes after dosing (the first time of sampling, 8.46 ug equivalents/mL). Radioactivity in plasma declined in a multi-exponential fashion; concentrations decreased rapidly to a mean of 0.057 ug equivalents/ml at 12 hours after dosing but thereafter declined more slowly, and were still detectable in all animals at 120 hours after dosing (mean, 0.013 ug equivalents/ml). Consideration of whole-blood and plasma concentrations indicated that radioactivity was cleared more slowly from blood cells than from plasma.

WHO/FAO: Expert Committee on Food Additives. Summary of Toxicological Data of Certain Food Additives Series 24: Trichlorogalactosucrose (1989). Available from, as of July 19, 2011: https://www.inchem.org/pages/jecfa.html


(14)C-trichlorogalactosucrose (1 mg/kg; 100 uCi > 98% pure) was given orally dissolved in water to 8 normal, healthy male volunteers and blood, urine and feces collected for up to 5 days after the dose. The total recovery of (14)C-activity was 92.7% (range 87.8-99.2%) with most of the radioactivity 78.3% (range 69.4-89.6%) in the feces, and the remainder 14.4% (range 8.8-21.7%) in the urine. The plasma concentrations of (14)C-activity reached a peak at about 2 hr after the dose, with levels of (14)C equivalent to approximately 250 ng/mL of trichlorogalactosucrose. The plasma concentrations fell rapidly between 2 and 12 hr followed by a more gradual decrease until 72 hr by which time the levels of radioactivity were near or below the limit of accurate determination. The mean 'effective half-life' calculated on the basis of a mean residence time (MRT) of 18.8 hr gives a value of 13.0 hr.

WHO/FAO: Expert Committee on Food Additives. Summary of Toxicological Data of Certain Food Additives Series 24: Trichlorogalactosucrose (1989). Available from, as of July 19, 2011: https://www.inchem.org/pages/jecfa.html


Three male subjects given a single oral dose (1.11 mg/kg b.w., 0.3 uCi/kg) of trichlorogalactosucrose uniformly labelled with carbon-14 excreted an average of 13.5% of the radioactivity in urine and 82.1% in feces in 5 days. No (14)CO2 was detected in expired air collected during the initial 8 hours after dosing. Maximum levels of radioactivity in the blood occurred within 2-3 hours and in two of the subjects declined with a half-life of approximately 2.5 hours. Chromatographic examination of the 0-3 hours urines indicated the presence of only a single radioactive component.

WHO/FAO: Expert Committee on Food Additives. Summary of Toxicological Data of Certain Food Additives Series 24: Trichlorogalactosucrose (1989). Available from, as of July 19, 2011: https://www.inchem.org/pages/jecfa.html


After single oral doses of (14)C-trichlorogalactosucrose to non-pregnant and pregnant rabbits at a dose level of 10 mg/kg, radioactivity was excreted mainly in the feces. During 24 hours after dosing, a mean of 16.8% of the dose was excreted in the feces of non-pregnant animals, increasing to 31.8% during 48 hours and 54.7% during 120 hours. Excretion of radioactivity in the feces of pregnant rabbits was similar, with means of 27.8%, 43.0% and 65.2% of the dose excreted by this route during 24, 48 and 120 hours after dosing, respectively. Means of 5.3% and 4.2% dose were excreted in the feces of non-pregnant and pregnant rabbits respectively during 96-120 hours after dosing, indicating that excretion of radioactivity was not completed after 5 days, probably because of the coprophagic behavior of rabbits. During 24 hours, means of 8.3% and 8.6% of the dose were excreted in the urine of non-pregnant and pregnant rabbits, respectively. Mean totals of 22.3% (non-pregnant rabbits) and 21.5% (pregnant rabbits) of the dose was gradually excreted in the urine during 5 days after dosing. Radioactivity was still being excreted in the urine of rabbits (up to 2.9% dose) during 96-120 hours after dosing. Mean total recoveries of radioactivity from the urine and feces of non- pregnant and pregnant rabbits after 5 days accounted for 80.3% and 87.0% of the dose respectively. The dose not accounted for was presumably still to be excreted since a total of up to 8.4% of the dose was excreted during 96-120 hours after dosing. There were no notable differences in the absorption and excretion of single oral doses of (14)C-trichlorogalactosucrose between non-pregnant and pregnant rabbits.

WHO/FAO: Expert Committee on Food Additives. Summary of Toxicological Data of Certain Food Additives Series 24: Trichlorogalactosucrose (1989). Available from, as of July 19, 2011: https://www.inchem.org/pages/jecfa.html


For more Absorption, Distribution and Excretion (Complete) data for Sucralose (14 total), please visit the HSDB record page.


4.3 Metabolism/Metabolites

Following a single oral dose of (14)C-sucralose (1mg/kg, 100 microCi) to eight male subjects, a mean of 14.5% (range 8.9 to 21.8%) of the radioactivity was excreted in urine and 78.3% (range 69.4 to 89.6%) in the feces, within 5 days. The total recovery of radioactivity averaged 92.8%. Plasma concentrations of radioactivity were maximal at about 2 hours after dosing. The mean residence time (MRT) for sucralose was 18.8 hr, while the effective half-life for the decline of plasma radioactivity was 13 hr. Two volunteers given a higher oral dose (10 mg/kg, 22.7 uCi) excreted a mean of 11.2% (9.6 and 12.7%) of the radioactivity in urine, and 85.5% (84.1 and 86.8%) in feces over 5 days. The total recovery of radioactivity was 96.7%. The radiolabelled material present in feces was essentially unchanged sucralose. Sucralose was the principal component in the urine together with two more polar components which accounted for only 2.6% of the administered dose (range 1.5 to 5.1% of dose); both metabolites possessed characteristics of glucuronide conjugates of sucralose.

PMID:10882816 Roberts A et al; Food Chem Toxicol 38 Suppl 2: S31-41 (2000)


4.4 Biological Half-Life

Three male subjects given a single oral dose (1.11 mg/kg b.w., 0.3 uCi/kg) of trichlorogalactosucrose uniformly labelled with carbon-14 excreted an average of 13.5% of the radioactivity in urine and 82.1% in feces in 5 days. ... Maximum levels of radioactivity in the blood occurred within 2-3 hours and in two of the subjects declined with a half-life of approximately 2.5 hours.

WHO/FAO: Expert Committee on Food Additives. Summary of Toxicological Data of Certain Food Additives Series 24: Trichlorogalactosucrose (1989). Available from, as of July 19, 2011: https://www.inchem.org/pages/jecfa.html


4.5 Mechanism of Action

Positive allosteric modulators of the human sweet taste receptor ...developed as a new way of reducing dietary sugar intake .../can be used as/ ...valuable tool molecules to study the general mechanism of positive allosteric modulations of T1R taste receptors. Using chimeric receptors, mutagenesis, and molecular modeling, .../the study/ reveal how ...sweet enhancers follow a similar mechanism as the natural umami taste enhancer molecules. Whereas the sweeteners bind to the hinge region and induce the closure of the Venus flytrap domain of T1R2, the enhancers bind close to the opening and further stabilize the closed and active conformation of the receptor.

PMID:20173095 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2842058 Zhang F, et al; Proc Natl Acad Sci USA 107 (10): 4752-4757 (2010)


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