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Chemistry

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Also known as: 541-02-6, Cyclopentasiloxane, decamethyl-, Cyclomethicone 5, 2,2,4,4,6,6,8,8,10,10-decamethyl-1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane, Dimethylsiloxane pentamer, Dekamethylcyklopentasiloxan
Molecular Formula
C10H30O5Si5
Molecular Weight
370.77  g/mol
InChI Key
XMSXQFUHVRWGNA-UHFFFAOYSA-N
FDA UNII
0THT5PCI0R

Decamethylcyclopentasiloxane
Cyclomethicone 5 is member of cyclomethicone, which are a group of liquid methyl siloxanes that have low viscosity and high volatility. Cyclomethicones are cyclic in structure with a monomer backbone of one silicon and two oxygen atoms bonded together. Cyclomethicone 5 is used in cosmetic and personal products as a skin emollient.
1 2D Structure

Decamethylcyclopentasiloxane

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,2,4,4,6,6,8,8,10,10-decamethyl-1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane
2.1.2 InChI
InChI=1S/C10H30O5Si5/c1-16(2)11-17(3,4)13-19(7,8)15-20(9,10)14-18(5,6)12-16/h1-10H3
2.1.3 InChI Key
XMSXQFUHVRWGNA-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C[Si]1(O[Si](O[Si](O[Si](O[Si](O1)(C)C)(C)C)(C)C)(C)C)C
2.2 Other Identifiers
2.2.1 UNII
0THT5PCI0R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. D5-sil

2.3.2 Depositor-Supplied Synonyms

1. 541-02-6

2. Cyclopentasiloxane, Decamethyl-

3. Cyclomethicone 5

4. 2,2,4,4,6,6,8,8,10,10-decamethyl-1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane

5. Dimethylsiloxane Pentamer

6. Dekamethylcyklopentasiloxan

7. Cyclomethicone

8. Ciclopentasiloxane

9. Cyclomethicone D5

10. 0tht5pci0r

11. Ddecamethylcyclopentasiloxane

12. Dow Corning 345 Fluid

13. 2,2,4,4,6,6,8,8,10,10-decamethyl-1,3,5,7,9,2,4,6,8,10-pentoxapentasilecane

14. Dow Corning 345

15. Nuc Silicone Vs 7158

16. Silicon Sf 1202

17. Cyclopentasiloxane, 2,2,4,4,6,6,8,8,10,10-decamethyl-

18. Cyclic Dimethylsiloxane Pentamer

19. Mfcd00046966

20. Union Carbide 7158 Silicone Fluid

21. Kf 995

22. Vs 7158

23. D5-sil

24. Ccris 1328

25. Hsdb 5683

26. Dekamethylcyklopentasiloxan [czech]

27. Einecs 208-764-9

28. Unii-0tht5pci0r

29. Decamethyl Cyclopentasiloxane

30. Sf 1202

31. Brn 1800166

32. D5 Cyclomethicone

33. D5

34. Dimethylcyclopentasiloxane

35. Decamethylcylopentasiloxane

36. Dsstox_cid_7184

37. Jeesilc Cps-211

38. Ec 208-764-9

39. Dsstox_rid_78338

40. Dsstox_gsid_27184

41. Schembl28497

42. N-propylheptamethyltrisiloxane

43. Xiameter Pmx-0245

44. 4-04-00-04128 (beilstein Handbook Reference)

45. Cyclopentasiloxane (d5)

46. Chembl1885178

47. Dtxsid1027184

48. Cyclopentasiloxane [inci]

49. Chebi:191092

50. Decamethylcyclopentasiloxane, 97%

51. Cyclomethicone 5 [usp-rs]

52. Cyclomethicone 5 [who-dd]

53. Bcp15826

54. Tox21_303170

55. Cd3770

56. Kf-995

57. Akos008901199

58. Zinc169743678

59. Cs-w009767

60. Db11244

61. Dow Corning St Cyclomethicone 5

62. Decamethylcyclopentasiloxane [mi]

63. Ncgc00163981-01

64. Ncgc00257224-01

65. Octamethylcyclotetrasiloxane (d5)

66. As-59731

67. Cas-541-02-6

68. Decamethylcyclopentasiloxane [hsdb]

69. Kp-545 Component Cyclomethicone 5

70. D1890

71. D3770

72. Decamethylcyclopentasiloxane (cyclic Monomer)

73. Ft-0665531

74. Dow Corning Up-1002 Ultra Pure Fluid

75. D78203

76. S05475

77. Decamethylcyclopentasiloxane, Analytical Standard

78. Q414350

79. Decamethyl-1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane

80. Cyclomethicone 5, United States Pharmacopeia (usp) Reference Standard

81. 2,2,4,4,6,6,8,8,10,10-decamethyl-1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane #

82. D5 Cyclomethicone, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 370.77 g/mol
Molecular Formula C10H30O5Si5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count0
Exact Mass370.09395673 g/mol
Monoisotopic Mass370.09395673 g/mol
Topological Polar Surface Area46.2 Ų
Heavy Atom Count20
Formal Charge0
Complexity258
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

To assess the fate of D5 absorbed from the skin in intact animals, (14)C-D5 was applied to the dorsal surface of male and female rats. Hair at the application site was clipped prior to application and the application site was covered with a non-occlusive elastic wrap. The study was designed to permit differentiation between D5 exhaled after absorption and D5 evaporating from the application site. After application of D5, the animals were transferred to metabolic cages for the collection of urine and feces. The majority (about 85%) of the applied (14)C-D5 volatilized from the skin. After 96 hr, 0.35% of the administered D5 remained at the application site and less than 1% of the applied (14)C-activity was recovered in urine and carcass with trace levels of (14)C-activity recovered in feces, CO2 traps, and tissues. The total amount of D5 absorbed was <1%.

Dekant W, Klaunig JE; Toxicology of decamethylcyclopentasiloxane (D5), Regulatory Toxicology and Pharmacology. p.2 (2015)


Octamethylcyclotetrasiloxane (D4) and decamethylcyclopentasiloxane (D5) are cyclic siloxanes used as chemical intermediates with some applications in consumer products. The in vitro percutaneous absorption of (14)C-D4 and (14)C-D5 was studied in flow-through diffusion cells. Single doses were applied neat and in antiperspirant formulations to dermatomed human skin for 24 hr. The majority of applied D4 and D5 (approximately 90%) volatilized before being absorbed. Only 0.5% of applied D4 was absorbed while the absorption of D5 (0.04%) was one order of magnitude lower. The largest percentage (>90%) of the absorbed D4 and D5 was found in the skin. The fate of D4 and D5 absorbed in the skin was studied in rat in vivo. A single dose of (14)C-D4 (10, 4.8 and 2 mg/sq cm) and (14)C-D5 (10 mg/sq cm) was topically applied inside a dosing chamber attached to the dorsal area. Rats were housed in metabolism cages up to 24 hr to enable collection of urine, feces, expired/escaped volatiles. The majority of applied D4 or D5 had volatilized from the skin surface. Less than 1.0% of the applied D4 and only 0.2% of applied D5 was absorbed with approximately 60% of absorbed D4 and 30% of absorbed D5 reaching systemic compartments. The amount absorbed into the skin decreased with time showing that residual D4 and D5 diffused back to the skin surface and continued to evaporate. Overall, a low tendency to pass through the skin into systemic compartments was demonstrated for both D4 (< or = 0.5% of applied dose) and D5 (<0.1% of applied dose).

PMID:18178298 Jovanovic ML et al; Regul Toxicol Pharmacol 50 (2): 239-48 (2008)


Toxicokinetic studies were performed in rats after dosing by gavage with (14)C-D5 (single dose of 1000 mg/kg bw) dissolved in different vehicles (corn oil and simethicone fluid) and as a neat material. The carrier had a significant influence on the extent of absorption of (14)C-D5. After administration of neat D5, approximately 10% of the dose was absorbed from the gastrointestinal tract. Based on blood area under the curve (AUC), absorption increased after administration of D5 in corn oil and decreased after administration in simethicone fluid. Elimination half-lives for D5-associated radioactivity in blood ranged from 45 (simethicone) to 240 hr (corn oil), and were between 117 (neat) and 242 hr (simethicone) for parent D5. The radioactivity eliminated in the urine consisted entirely of polar metabolites of D5. Mass balance analysis indicated that approximately 60-80 % of the administered D5 was excreted unchanged in the feces, and up to 20% of administered D5 as water soluble metabolites in urine. Half of the systemically available D5 was eliminated as unchanged D5 in exhaled air. However, the kinetics and tissue distribution observed after oral dosing were qualitatively different from the distributions after inhalation or dermal exposures. Higher relative concentrations of D5 were noted in liver and spleen as compared to exposure to D5 by inhalation and dermal application.

Dekant W, Klaunig JE; Toxicology of decamethylcyclopentasiloxane (D5), Regulatory Toxicology and Pharmacology. p.2 (2015)


Separate 77-d fish feeding studies were conducted on the cyclic volatile methylsiloxane (cVMS) chemicals octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane with the rainbow trout, Oncorhynchus mykiss, with the determination of biomagnification factor (BMF) and lipid-adjusted BMF (BMF(L)) values as the final experimental metrics. The studies used fish food concentrations of about 500 ug/g for exposure periods of 35 d, followed by a depuration period of 42 d with clean food. The fish tissue concentrations of D4 and D5 achieved empirical steady-state by day 21 in each study. By day 7 of exposure, total (14)C activity of both compounds had moved from the fish gastrointestinal (GI) tract into surrounding tissue. An absence of significant fish growth during the initial depuration phase allowed for measurement of empirical depuration rate constants (k2) independent of growth dilution for D4 and D5 of 0.035 and 0.040/d, respectively, corresponding to elimination half-lives of approximately 20d. These rate constants indicated that about 70-75% of steady-state was achieved during exposure in both studies, resulting in empirical steady-state BMF and BMF(L) values of 0.28 and 0.66 for D4, respectively, and 0.32 and 0.85 for D5, respectively. Kinetic modeling using simple first-order uptake and depuration dynamics produced good agreement with experimental data, with D4 and D5 assimilation efficiencies of 40% and 44%, respectively. Growth-corrected depuration rate constants modeled over the entire study data set indicated slower elimination kinetics for D4 (k2 of 0.007/d or half-life of 100 d) compared to D5 (k2 of 0.010/d or elimination half-life of 69 d). Kinetic BMFk values (i.e., k1/k2) for D4 and D5 were 1.7 and 1.3, respectively, with lipid-adjusted BMFk(L) values of 4.0 and 3.4, respectively.

PMID:23200569 Woodburn K et al; Chemosphere 93 (5): 779-88 (2013)


For more Absorption, Distribution and Excretion (Complete) data for DECAMETHYLCYCLOPENTASILOXANE (13 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

Major metabolites of D5 were identified in urine collected from Fischer (F-344) rats administered ... (14)C-D5 orally and via intravenous injection ... The metabolites of D5 are as follows: Me(2)Si(OH)(2), MeSi(OH)(3), MeSi(OH)(2)OSi(OH)(3), MeSi(OH)(2)OSi(OH)(2)Me, MeSi(OH)(2)OSi(OH)Me(2), Me(2)Si(OH)OSi(OH)Me(2), Me(2)Si(OH)OSiMe(2)OSi(OH)Me(2), nonamethylcyclopentasiloxanol, and hydroxymethylnonamethylcyclopentasiloxane. No parent ... D5 was present in urine. The presence of certain metabolites such as ... Me(2)Si(OH)(2) ... clearly established the occurrence of demethylation at the silicon-methyl bonds. Metabolites of the linear siloxane are structurally different from that obtained for cyclic siloxane except for the commonly present Me(2)Si(OH)(2). Mechanistic pathways for the formation of the metabolites were proposed.

PMID:12527702 Varaprath S et al; Drug Metab Dispos 31 (2): 206-14 (2003)


4.3 Biological Half-Life

Toxicokinetic studies were performed in rats after dosing by gavage with (14)C-D5 (single dose of 1000 mg/kg bw) dissolved in different vehicles (corn oil and simethicone fluid) and as a neat material. The carrier had a significant influence on the extent of absorption of (14)C-D5. ... Half of the systemically available D5 was eliminated as unchanged D5 in exhaled air. ...

Dekant W, Klaunig JE; Toxicology of decamethylcyclopentasiloxane (D5), Regulatory Toxicology and Pharmacology. p.2 (2015)


Separate 77-d fish feeding studies were conducted on the cyclic volatile methylsiloxane (cVMS) chemicals octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane with the rainbow trout, Oncorhynchus mykiss, with the determination of biomagnification factor (BMF) and lipid-adjusted BMF (BMF(L)) values as the final experimental metrics. The studies used fish food concentrations of about 500 ug/g for exposure periods of 35 d, followed by a depuration period of 42 d with clean food. ... An absence of significant fish growth during the initial depuration phase allowed for measurement of empirical depuration rate constants (k2) independent of growth dilution for D4 and D5 of 0.035 and 0.040/d, respectively, corresponding to elimination half-lives of approximately 20d.

PMID:23200569 Woodburn K et al; Chemosphere 93 (5): 779-88 (2013)


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04-Oct-2023
21-Sep-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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