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346861

Sigma-Aldrich

(S)-(−)-5-Hydroxymethyl-2(5H)-furanone

98%

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About This Item

Empirical Formula (Hill Notation):
C5H6O3
CAS Number:
78508-96-0
Molecular Weight:
114.10
Beilstein:
3537455
MDL number:
MFCD00075370
UNSPSC Code:
12352005
PubChem Substance ID:
24861447
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D −144°, c = 1 in H2O

mp

41-43 °C (lit.)

functional group

ester
hydroxyl

storage temp.

2-8°C

SMILES string

OC[C@H]1OC(=O)C=C1

InChI

1S/C5H6O3/c6-3-4-1-2-5(7)8-4/h1-2,4,6H,3H2/t4-/m0/s1

InChI key

AWNLUIGMHSSXHB-BYPYZUCNSA-N

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Application

(S)-(−)-5-Hydroxymethyl-2(5H)-furanone can be used as a starting material in the preparation of:
  • Partially saturated heterocycles via a diastereoselective ring chain formation.
  • A natural product named (+)-muscarine.
  • 3′-Ethynylthymidine as a possible antiviral agent.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

346861-1G:
346861-250MG:
346861-BULK:
346861-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC1354V
1423737V
1432919
1423737
1416855

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Bohrisch, J. et al.
Tetrahedron Letters, 34, 2749-2749 (1993)
Synthesis of (+)-muscarine from (S)-(-)-5-hydroxymethyl-2 (5H)-furanone
Kang KH, et al.
Tetrahedron Letters, 41(42), 8137-8140 (2000)

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