Sinigrin

Names

[ Name ]:
Sinigrin

[Synonym ]:
(−)-Sinigrin hydrate
Allyl glucosinolate
Kalium-[({[(1Z)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]sulfanyl}-3-buten-1-yliden]amino}oxy)sulfonyl]oxidanid
Kalium-1-S-[(1Z)-N-(sulfonatooxy)-3-butenimidoyl]-1-thio-β-D-glucopyranose
Myronate Potassium
1-Thio-b-D-glucopyranose 1-[N-(Sulfooxy)-3-butenimidate] Monopotassium Salt
Potassium Myronate
[({[(1Z)-1-{[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]sulfanyl}-3-butèn-1-ylidène]amino}oxy)sulfonyl]oxidanide de potassium
Potassium 1-S-[(1Z)-N-(sulfonatooxy)-3-butenimidoyl]-1-thio-β-D-glucopyranose
Potassium [({[(1Z)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]sulfanyl}-3-buten-1-ylidene]amino}oxy)sulfonyl]oxidanide
MFCD00149447
Sinigroside
EINECS 223-545-8
Potassium 1-S-[(1E)-N-(sulfonatooxy)-3-butenimidoyl]-1-thio-β-D-glucopyranose hydrate (1:1:1)
1-S-[(1Z)-N-(Sulfonatooxy)-3-butènan-1-imidoyl]-1-thio-β-D-glucopyranose de potassium
Sinigrin Hydrate
β-D-Glucopyranose, 1-S-[(1E)-1-[(sulfooxy)imino]-3-buten-1-yl]-1-thio-, potassium salt, hydrate (1:1:1)
Sinigrin
Potassium 1-S-[(1Z)-N-(sulfonatooxy)but-3-enimidoyl]-1-thio-β-D-glucopyranose
β-D-Glucopyranose, 1-S-[(1Z)-1-[(sulfooxy)imino]-3-buten-1-yl]-1-thio-, potassium salt (1:1)

Biological Activity

[Description]:

Sinigrin is a major glucosinolate present in plants of the Brassicaceae family, with anti-adipogenic effects[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[References]

[1]. Lee HW, et al. Inhibitory effect of sinigrin on adipocyte differentiation in 3T3-L1 cells: Involvement of AMPK and MAPK pathways. Biomed Pharmacother. 2018 Jun;102:670-680.

Chemical & Physical Properties

[ Melting Point ]:
128 (dec.)(lit.)ºC

[ Molecular Formula ]:
C₁₀H₁₆KNO₉S₂

[ Molecular Weight ]:
415.479

[ Exact Mass ]:
415.000916

[ PSA ]:
202.62000

[ Water Solubility ]:
almost transparency

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LZ5778000

CHEMICAL NAME :: Glucopyranose, 1-thio-, 1-(3-butenohydroximate) NO-(hydrogensulfate), monopotassium salt, beta-D-

CAS REGISTRY NUMBER :: 3952-98-5

LAST UPDATED :: 199712

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C10-H16-N-O9-S2.K

MOLECULAR WEIGHT :: 397.49

WISWESSER LINE NOTATION :: T6OTJ BSY2U1&UNOSWO CQ DQ EQ F1Q &-KA-

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 644 mg/kg

SEX/DURATION :: female 8-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 644 mg/kg

SEX/DURATION :: female 8-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 4600 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 348,19,1995

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LZ5778000

[ HS Code ]:
29389090

Precursor & DownStream

Precursor

DownStream

Articles

Interactive effects of sulfur and nitrogen supply on the concentration of sinigrin and allyl isothiocyanate in Indian mustard (Brassica juncea L.).

J. Agric. Food Chem. 57(9) , 3837-44, (2009)

Food derived from Brassica species is rich in glucosinolates. Hydrolysis of these compounds by myrosinase yields isothiocyanates and other breakdown products, which due to their pungency represent the...

Multidirectional time-dependent effect of sinigrin and allyl isothiocyanate on metabolic parameters in rats.

Plant Foods Hum. Nutr. 65(3) , 217-24, (2010)

Sinigrin (SIN) and allyl isothiocyanate (AITC) are compounds found in high concentrations in Brassica family vegetables, especially in Brussels sprouts. Recently, they have been used as a nutrition su...

Allyl isothiocyanate-rich mustard seed powder inhibits bladder cancer growth and muscle invasion.

Carcinogenesis 31(12) , 2105-10, (2010)

Allyl isothiocyanate (AITC), which occurs in many common cruciferous vegetables, was recently shown to be selectively delivered to bladder cancer tissues through urinary excretion and to inhibit bladd...