D-Phenylalanine

HCID 71567CAS 673-06-3

Basic information

Standard SMILES
N[C@H](Cc1ccccc1)C(=O)O
InChIKey
COLNVLDHVKWLRT-MRVPVSSYSA-N
Molecular formula
C9H11NO2
Average molar mass
165.19 g/mol
Monoisotopic mass
165.07897859

Names & identifiers

Preferred name
D-Phenylalanine
IUPAC
(2R)-2-amino-3-phenylpropanoic acid
English name
D-Phenylalanine
Molecular formula
C9H11NO2
Molecular weight
165.19

Names & synonyms

D-phenylalanine(2R)-2-amino-3-phenylpropanoic acidSabidenD-PheAlanine, phenyl-, D-D-(+)-PhenylalanineD-alpha-Amino-beta-phenylpropionic acidNCI-C60195CCRIS 6267EINECS 211-603-5UNII-032K16VRCUNSC 25005
Show more names
PHENYLALANINEH-D-PHE-OHD-Phe-OHEndorphenylD-PhenylalaninD(+)-PHENYLALANINE(R)-2-amino-3-phenylpropanoic acid
(R)-PHENYLALANINEPHENYLALANINE, D-DTXSID4025876CHEBI:16998D-PHENYLALANINE [WHO-DD]D-.beta.-Phenyl-.alpha.-alanineNSC-25005D-phenylalanine zwitterion

Database identifiers

CAS
673-06-3
PubChem CID
71567
DTXSID
DTXSID4025876
ChEMBL
CHEMBL379630
ChEBI
CHEBI:16998
UNII
032K16VRCU
EC Number
211-603-5
Nikkaji
J9.200B

Properties

Computed structural properties

XLogP
-1.5
Topological polar surface area
63.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
12

Experimental & physicochemical properties

Solubility · 2 items

Soluble (NTP, 1992)

28200

Boiling Point563 °F at 760 mmHg (Sublimes) (NTP, 1992)
Melting Point541 to 543 °F (Decomposes) (NTP, 1992)
Physical DescriptionD-phenylalanine appears as needles or prisms. (NTP, 1992)
Collision Cross Section · 1 item

136.75 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];134.07 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];138.83 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
273 · 273-276 °C(lit.)
alpha
33.5 · 33.5 º (c=2, H2O)
Boiling point
293.03 °C · 293.03°C (rough estimate)
Density
1.1603 · 1.1603 (rough estimate)
refractive index
34 ° · 34 ° (C=2, H2O)
storage temp.
Store at RT.

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 80% (12 of 15) of all reports.

Warning

H315 (13.3%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (13.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (13.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 15 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 12 of 15 reports by companies.;There are 3 notifications provided by 3 of 15 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 17-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/22600

D-Phenylalanine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Fire HazardsFlash point data for this chemical are not available, however it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: This compound may cause irritation.;ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of carbon monoxide, carbon dioxide and NOx. (NTP, 1992)
Reactive GroupSalts, Acidic
Reactivity ProfileD-PHENYLALANINE may be light sensitive. This compound reacts with strong oxidizing agents, acids and bases. (NTP, 1992). It acts as a weak acid in solution.
Air and Water ReactionsWater soluble. Aqueous solutions are weakly acidic.

Safety & protection

Fire FightingFires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter.;RECOMMENDED GLOVE MATERIALS: Permeation data indicate that latex gloves may provide protection from contact with this compound. Latex over latex gloves is recommended. However, if this chemical makes direct contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992)

Regulatory information

Regulatory Information · 2 items

Status: Active Update: 17-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/22600

D-Phenylalanine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
AY7533000
hs_code
29224995
Toxicity
TDLo orl-hmn: 500 mg/kg/5W-I:GIT JACTDZ 1(3),124,82

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationD-Phenylalanine: ACTIVE
Applications · 4 items

DescriptionD-phenylalanine is an inhibitor of enzymes that inactivate enkephalins. Enkephalins are naturally occurring morphine-like peptides that function to reduce pain. By blocking enzymes from degrading enkephalins, D-phenylalanine can reduce pain severity. Phenylalanine is the only amino acid other than methionine in which both isomers, L and D, are readily absorbed. DLPA is 50% D-phenylalanine and 50% L-phenylalanine, making it clinically useful as a neurotransmitter precursor and as a potential pain mediator.Phenylalanine is found in three different forms. The natural form, found in food, is also called L-phenylalanine. There’s also a synthetic form, D-phenylalanine, which is very similar to the natural version. Both of these forms come with their own unique benefits, but if you want to get the most out of them, you’ll want to look at the third form: DL-phenylalanine. This form combines both the “L” and “D” forms, creating a supplement with the benefits of both types.

DescriptionD-Phenylalanine, also known as D-alpha-Amino-beta-phenylpropionic acid, is a kind of non-proteinogenic amino acid. The biological function of D-phenylalanine remains unclear. However, it has certain anti-depressant, analgesic activities and pharmacological activity at niacin receptor II. The mechanism action of its analgesic activity seems to originate from its inhibition of enkephalin degradation by the carboxypeptidase A. Enkephalins are part of your body’s natural pain relief system. When they are broken down by enkephalinase, this contributes to the sensation of pain. D-Phenylalanine is specifically thought to be beneficial for reducing feelings of chronic pain. D-phenylalanine has been used with mixed results to treat chronic pain, including pain caused by rheumatoid arthritis. The primary use of D-phenylalanine as a health supplement is the relief of discomfort.

UsesD-Phenylalanine, the stereoisomer of L-Phenylalanine (P319415) has been used in the synthesis of Schaeffer’s acid analogues as important structures in tuberculostatic design. They exhibit the ability to inhibit Mycobacterium tuberculosis type II dehydroquinase.

General DescriptionD-phenylalanine appears as needles or prisms.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
黄冈森阳化工有限公司0713-8205211 17671088222 · [email protected]
Additional notes · 1 item

DefinitionChEBI: D-phenylalanine is the D-enantiomer of phenylalanine. It is a phenylalanine and a D-alpha-amino acid. It is a conjugate base of a D-phenylalaninium. It is a conjugate acid of a D-phenylalaninate. It is an enantiomer of a L-phenylalanine. It is a tautomer of a D-phenylalanine zwitterion.

Related reactions

110 records

Linked notes

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