D-(-)-Pantolactone - 99%, high purity , CAS No.599-04-2

  • ≥99%
Item Number
P122332
Grouped product items
SKUSizeAvailabilityPrice Qty
P122332-5g
5g
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$9.90
P122332-25g
25g
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$19.90
P122332-100g
100g
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$59.90
P122332-500g
500g
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$129.90

Basic Description

SynonymsAC1149 | D-Pantolactone | PANTOLACTONE, (-)- | UNII-J288D7O0JS | dihydro-3-hydroxy-4,4-dimethyl- 2(3H)-Furanone | D-(?)-Pantolactone | HY-W010396 | PANTOLACTONE [MI] | pantoyl lactone | s6027 | PANTOLACTONE, R-ISOMER | Z1065885480 | bmse000381 | 2(3H)-Fur
Specifications & Purity≥99%
Storage TempStore at 2-8°C,Argon charged
Shipped InWet ice
Product Description

D-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions.

It can be used as a chiral starting material to synthesize:

• An insect sex pheromone named 1S,2S,3R-1-acetoxymethyl-2,3,4,4-tetrameth-ylcyclopentane.

• (-)-Enantiomer of (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, a norsesquiterpene alkaloid.

• A bicyclic diterpene named isofregenedadio

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name (3R)-3-hydroxy-4,4-dimethyloxolan-2-one
INCHI InChI=1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1
InChi Key SERHXTVXHNVDKA-BYPYZUCNSA-N
Canonical SMILES CC1(COC(=O)C1O)C
Isomeric SMILES CC1(COC(=O)[C@@H]1O)C
WGK Germany 1
PubChem CID 439368
Molecular Weight 130.14
Beilstein 24854272
Reaxy-Rn 3588195

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

9 results found

Lot NumberCertificate TypeDateItem
D2402399Certificate of AnalysisMar 20, 2024 P122332
D2402400Certificate of AnalysisMar 20, 2024 P122332
D2402401Certificate of AnalysisMar 20, 2024 P122332
D2402402Certificate of AnalysisMar 20, 2024 P122332
D2402403Certificate of AnalysisMar 20, 2024 P122332
A1507060Certificate of AnalysisSep 21, 2022 P122332
K1812054Certificate of AnalysisSep 15, 2022 P122332
E1814027Certificate of AnalysisMar 08, 2022 P122332
H2310025Certificate of AnalysisMar 20, 2021 P122332

Chemical and Physical Properties

SensitivityMoisture Sensitive
Specific Rotation[α][α]25/D −49.8°, c = 2 in H2O
Boil Point(°C)120-122°C/15mm
Melt Point(°C)92°C

Safety and Hazards(GHS)

Pictogram(s) GHS07
Signal Warning
Hazard Statements

H319:Causes serious eye irritation

Precautionary Statements

P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing.

P280:Wear protective gloves/protective clothing/eye protection/face protection.

P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes.

P337+P317:If eye irritation persists: Get medical help.

WGK Germany 1
Reaxy-Rn 3588195
Merck Index 7013

Related Documents

Citations of This Product

1. Xiao-Jian Zhang, Min Cao, Yi-Fei Luo, Meng-Yu Huang, Fang-Ying Zhu, Zhi-Qiang Liu, Yu-Guo Zheng.  (2023)  Efficient synthesis of D-pantolactone in monophase and organic-aqueous biphase reaction biosystem using a novel conjugated polyketide reductase based on integrated substrate pocket alteration.  BIOCHEMICAL ENGINEERING JOURNAL,    (109088).  [PMID:19605561] [10.1016/j.bej.2023.109088]
2. Yaling Huang, Junwen Wan, Min Sun, Tao Feng, Qian Liu, Shiqing Song, Xiaoming Zhang, Chi-Tang Ho.  (2023)  Flavor profile disclosure of Chinese steamed breads (CSBs) by sensomics approach.  Food Bioscience,  51  (102198).  [PMID:] [10.1016/j.fbio.2022.102198]

References

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2. A D Keefe,G L Newton,S L Miller.  (1995-02-23)  A possible prebiotic synthesis of pantetheine, a precursor to coenzyme A..  Nature,  373  ((6516)): (683-685).  [PMID:7854449]
3. A Takasu,K Ohya.  (1987-02-27)  Separation and determination of the enantiomers of pantolactone by gas-liquid chromatography..  Journal of chromatography,  389  ((1)): (251-255).  [PMID:3571352]
4. A G Moĭseenok,V S Slyshenkov,E V Sunozova,V A Gurinovich.  (1984-01-01)  [Quantitative gas chromatographic determination of pantolactone]..  Voprosy meditsinskoi khimii,  30  ((1)): (126-128).  [PMID:6710930]
5. S Shimizu,M Kataoka.  (1996-10-12)  Optical resolution of pantolactone by a novel fungal enzyme, lactonohydrolase..  Annals of the New York Academy of Sciences,  799  (650-658).  [PMID:8958119]
6. J Ogawa,S Shimizu.  (1999-03-31)  Microbial enzymes: new industrial applications from traditional screening methods..  Trends in biotechnology,  17  ((1)): (13-21).  [PMID:10098273]
7. S L Miller,G Schlesinger.  (1993-04-01)  Prebiotic syntheses of vitamin coenzymes: II. Pantoic acid, pantothenic acid, and the composition of coenzyme A..  Journal of molecular evolution,  36  ((4)): (308-314).  [PMID:11536535]
8. A D Keefe,S L Miller.  (1996-02-01)  Potentially prebiotic syntheses of condensed phosphates..  Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life,  26  ((1)): (15-25).  [PMID:11536744]
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10. Michael-Rock Goldsmith,Nilu Jayasuriya,David N Beratan,Peter Wipf.  (2003-12-18)  Optical rotation of noncovalent aggregates..  Journal of the American Chemical Society,  125  ((51)): (15696-15697).  [PMID:14677931]
11. Bala Rathinasabapathi,Suresh Babu Raman.  (2005-03-16)  Exogenous supply of pantoyl lactone to excised leaves increases their pantothenate levels..  Annals of botany,  95  ((6)): (1033-1037).  [PMID:15767268]
12. Keiji Sakamoto,Kohsuke Honda,Koichi Wada,Shinji Kita,Kazuya Tsuzaki,Hanae Nose,Michihiko Kataoka,Sakayu Shimizu.  (2005-06-07)  Practical resolution system for DL-pantoyl lactone using the lactonase from Fusarium oxysporum..  Journal of biotechnology,  118  ((1)): (99-106).  [PMID:15935504]
13. Paul R Blakemore,Cindy C Browder,Jian Hong,Christopher M Lincoln,Pavel A Nagornyy,Lonnie A Robarge,Duncan J Wardrop,James D White.  (2005-07-02)  Total synthesis of polycavernoside A, a lethal toxin of the red alga Polycavernosa tsudai..  The Journal of organic chemistry,  70  ((14)): (5449-5460).  [PMID:15989326]
14. Zhiqiang Liu,Zhihao Sun,Yong Leng.  (2006-08-03)  Directed evolution and characterization of a novel D-pantonohydrolase from Fusarium moniliforme..  Journal of agricultural and food chemistry,  54  ((16)): (5823-5830).  [PMID:16881683]
15. Ulrich Klar,Bernd Buchmann,Wolfgang Schwede,Werner Skuballa,Jens Hoffmann,Rosemarie B Lichtner.  (2006-09-29)  Total synthesis and antitumor activity of ZK-EPO: the first fully synthetic epothilone in clinical development..  Angewandte Chemie (International ed. in English),  45  ((47)): (7942-7948).  [PMID:17006870]
16. Pelayo Camps,Tània Gómez,Diego Muñoz-Torrero,Jordi Rull,Laura Sánchez,Francesca Boschi,Mauro Comes-Franchini,Alfredo Ricci,Teresa Calvet,Mercè Font-Bardia,Erik De Clercq,Lieve Naesens.  (2008-07-30)  Synthesis and absolute configuration of novel N,O-psiconucleosides using (R)-N-phenylpantolactam as a resolution agent..  The Journal of organic chemistry,  73  ((17)): (6657-6665).  [PMID:18661943]
17. Bing Chen,Li-Qiang Fan,Jian-He Xu,Jian Zhao,Xian Zhang,Li-Ming Ouyang.  (2009-10-31)  Biocatalytic properties of a recombinant Fusarium proliferatum lactonase with significantly enhanced production by optimal expression in Escherichia coli..  Applied biochemistry and biotechnology,  162  ((3)): (744-756).  [PMID:19876606]
18. Atul K Hajare,Velayutham Ravikumar,Shaik Khaleel,Debnath Bhuniya,D Srinivasa Reddy.  (2011-01-05)  Synthesis of molluscicidal agent cyanolide a macrolactone from D-(-)-pantolactone..  The Journal of organic chemistry,  76  ((3)): (963-966).  [PMID:21192736]
19. Dayong Si,Nobuyuki Urano,Shinya Nozaki,Kohsuke Honda,Sakayu Shimizu,Michihiko Kataoka.  (2012-03-09)  L-pantoyl lactone dehydrogenase from Rhodococcus erythropolis: genetic analyses and application to the stereospecific oxidation of L-pantoyl lactone..  Applied microbiology and biotechnology,  95  ((2)): (431-440).  [PMID:22398860]
20. Dayong Si,Nobuyuki Urano,Sakayu Shimizu,Michihiko Kataoka.  (2012-09-04)  LplR, a repressor belonging to the TetR family, regulates expression of the L-pantoyl lactone dehydrogenase gene in Rhodococcus erythropolis..  Applied and environmental microbiology,  78  ((22)): (7923-7930).  [PMID:22941082]
21. Cheryl N Miller,Eric D LoVullo,Todd M Kijek,James R Fuller,Jason C Brunton,Shaun P Steele,Sharon A Taft-Benz,Anthony R Richardson,Thomas H Kawula.  (2012-12-18)  PanG, a new ketopantoate reductase involved in pantothenate synthesis..  Journal of bacteriology,  195  ((5)): (965-976).  [PMID:23243306]
22. Matthew B Kubilius,Raymond S Tu.  (2017-11-21)  Circular Dichroistic Impacts of 1-(3-Dimethylaminopropyl)-3-ethylurea: Secondary Structure Artifacts Arising from Bioconjugation Using 1-Ethyl-3-[3-dimethylaminopropyl]carbodiimide..  ACS omega,  ((11)): (8308-8312).  [PMID:31457370]
23. Hung-Wei Tsui,Pei-Wen Ye,Si-Xian Huang.  (2021-01-03)  Effect of solvents on the chiral recognition mechanisms of immobilized cellulose-based chiral stationary phase..  Journal of chromatography. A,  1637  (461796-461796).  [PMID:33387913]
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25. M Kataoka,A-R G Delacruz-Hidalgo,M A Akond,E Sakuradani,K Kita,S Shimizu.  (2003-11-01)  Gene cloning and overexpression of two conjugated polyketone reductases, novel aldo-keto reductase family enzymes, of Candida parapsilosis..  Applied microbiology and biotechnology,  64  ((3)): (359-366).  [PMID:14593510]
26. Morris Markert,Ulf Scheffler,Rainer Mahrwald.  (2009-11-03)  Asymmetric histidine-catalyzed cross-aldol reactions of enolizable aldehydes: access to defined configured quaternary stereogenic centers..  Journal of the American Chemical Society,  131  ((46)): (16642-16643).  [PMID:19877634]
27. Xiao-Jian Zhang, Min Cao, Yi-Fei Luo, Meng-Yu Huang, Fang-Ying Zhu, Zhi-Qiang Liu, Yu-Guo Zheng.  (2023)  Efficient synthesis of D-pantolactone in monophase and organic-aqueous biphase reaction biosystem using a novel conjugated polyketide reductase based on integrated substrate pocket alteration.  BIOCHEMICAL ENGINEERING JOURNAL,    (109088).  [PMID:19605561] [10.1016/j.bej.2023.109088]
28. Yaling Huang, Junwen Wan, Min Sun, Tao Feng, Qian Liu, Shiqing Song, Xiaoming Zhang, Chi-Tang Ho.  (2023)  Flavor profile disclosure of Chinese steamed breads (CSBs) by sensomics approach.  Food Bioscience,  51  (102198).  [PMID:] [10.1016/j.fbio.2022.102198]

Solution Calculators